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_4518113
_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            'C13 H19 F N2 O2'
_chemical_formula_weight         254.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 101.5840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8985(2)
_cell_length_b                   7.4145(2)
_cell_length_c                   15.3304(3)
_cell_measurement_reflns_used    8495
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.2297
_cell_measurement_theta_min      4.3092
_cell_volume                     1324.92(5)
_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    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 7.3910
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16859
_diffrn_reflns_theta_full        68.28
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         5.89
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_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    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0602P)^2^+0.9516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                2015
_reflns_number_total             2406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03278_si_002.cif
_cod_data_source_block           glo9721
_cod_database_code               4518113
_shelx_res_checksum              25977
_shelx_hkl_checksum              67837