Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
Supranovich, Vyacheslav I.; Dmitriev, Igor A.; Dilman, Alexander D.; Beilstein Journal of Organic Chemistry 16 (2020) 3104–3108; doi:10.3762/bjoc.16.260

data_4038941
_publ_section_title
;
 Synthesis of tetrafluorinated piperidines from nitrones via a
 visible-light-promoted annelation reaction
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              3104
_journal_page_last               3108
_journal_paper_doi               10.3762/bjoc.16.260
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C13 H15 F4 N S'
_chemical_formula_sum            'C13 H15 F4 N S'
_chemical_formula_weight         293.32
_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_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.2710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2686(3)
_cell_length_b                   7.4126(2)
_cell_length_c                   13.3406(3)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.81
_cell_measurement_theta_min      3.06
_cell_volume                     1309.97(5)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59051
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.325
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.6967
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         6357
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.4993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5116
_reflns_number_total             6357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-260-S2.cif
_cod_data_source_block           SU1089
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038941
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              742
_shelx_hkl_checksum              29622