Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
Wagener, Tobias; Heusler, Arne; Nairoukh, Zackaria; Bergander, Klaus; Daniliuc, Constantin G.; Glorius, Frank; ACS Catalysis  (2020) 12052–12057; doi:10.1021/acscatal.0c03278

data_4518110
_publ_section_title
;
 Accessing (Multi)Fluorinated Piperidines Using Heterogeneous
 Hydrogenation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              12052
_journal_page_last               12057
_journal_paper_doi               10.1021/acscatal.0c03278
_journal_year                    2020
_chemical_formula_sum            'C5 H8 F N O'
_chemical_formula_weight         117.12
_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   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 93.296(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8234(8)
_cell_length_b                   7.0364(7)
_cell_length_c                   11.2928(13)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.5191
_cell_measurement_theta_min      6.4972
_cell_volume                     541.29(10)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7570
_diffrn_reflns_theta_full        66.55
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         6.50
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.3467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                833
_reflns_number_total             956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03278_si_002.cif
_cod_data_source_block           glo9673
_cod_database_code               4518110
_shelx_res_checksum              62476
_shelx_hkl_checksum              97663