#------------------------------------------------------------------------------
#$Date: 2020-10-03 00:23:57 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518113.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518113
loop_
_publ_author_name
'Wagener, Tobias'
'Heusler, Arne'
'Nairoukh, Zackaria'
'Bergander, Klaus'
'Daniliuc, Constantin G.'
'Glorius, Frank'
_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/[σ²(Fo²)+(0.0602P)²+0.9516P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            cs0c03278_si_002.cif
_cod_data_source_block           glo9721
_cod_database_code               4518113
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.81703(10) 0.26399(16) 0.44132(8) 0.0363(3) Uani d . . . 1 . .
N N1 0.71234(15) 0.5902(2) 0.36108(12) 0.0303(4) Uani d . . . 1 . .
H H1A 0.658(2) 0.645(4) 0.3174(18) 0.048(7) Uiso d . . . 1 . .
N N2 0.53358(18) 0.0206(2) 0.38376(14) 0.0407(5) Uani d . . . 1 . .
H H2A 0.560(2) -0.007(3) 0.3370(18) 0.040(7) Uiso d . . . 1 . .
H H2B 0.513(2) -0.068(4) 0.4165(19) 0.049(7) Uiso d . . . 1 . .
O O1 0.49403(12) 0.23877(18) 0.47551(9) 0.0325(4) Uani d . . . 1 . .
C C1 0.65659(17) 0.4664(3) 0.41488(13) 0.0290(4) Uani d . . . 1 . .
H H1 0.6059 0.539 0.4462 0.035 Uiso calc U . R 1 . .
C C2 0.74854(17) 0.3773(3) 0.48464(13) 0.0320(5) Uani d . . . 1 . .
H H2 0.7106 0.3017 0.5244 0.038 Uiso calc U . R 1 . .
C C3 0.82601(18) 0.5130(3) 0.54078(14) 0.0364(5) Uani d . . . 1 . .
H H3A 0.8906 0.4488 0.5791 0.044 Uiso calc U . R 1 . .
H H3B 0.7824 0.5767 0.58 0.044 Uiso calc U . R 1 . .
C C4 0.87336(18) 0.6505(3) 0.48335(14) 0.0354(5) Uani d . . . 1 . .
H H4A 0.9157 0.7459 0.5217 0.042 Uiso calc U . R 1 . .
H H4B 0.9274 0.5905 0.4512 0.042 Uiso calc U . R 1 . .
C C5 0.77517(18) 0.7340(3) 0.41682(14) 0.0338(5) Uani d . . . 1 . .
H H5A 0.7228 0.7985 0.4488 0.041 Uiso calc U . R 1 . .
H H5B 0.8056 0.8221 0.3789 0.041 Uiso calc U . R 1 . .
C C6 0.58158(17) 0.3304(3) 0.35371(13) 0.0282(4) Uani d . . . 1 . .
H H6 0.6309 0.2659 0.3181 0.034 Uiso calc U . R 1 . .
C C7 0.53322(17) 0.1912(3) 0.41033(13) 0.0286(4) Uani d . . . 1 . .
C C8 0.48320(16) 0.4191(2) 0.28966(12) 0.0259(4) Uani d . . . 1 . .
C C9 0.40590(17) 0.5329(3) 0.32053(13) 0.0288(4) Uani d . . . 1 . .
H H9 0.4165 0.5592 0.3823 0.035 Uiso calc U . R 1 . .
C C10 0.31388(18) 0.6077(3) 0.26168(13) 0.0321(5) Uani d . . . 1 . .
H H10 0.2615 0.6839 0.2835 0.039 Uiso calc U . R 1 . .
C C11 0.29776(18) 0.5719(3) 0.17098(14) 0.0331(5) Uani d . . . 1 . .
H H11 0.2343 0.6224 0.1309 0.04 Uiso calc U . R 1 . .
C C12 0.37493(19) 0.4620(3) 0.13958(14) 0.0342(5) Uani d . . . 1 . .
H H12 0.3652 0.4389 0.0776 0.041 Uiso calc U . R 1 . .
C C13 0.46663(18) 0.3855(3) 0.19859(13) 0.0306(4) Uani d . . . 1 . .
H H13 0.5187 0.3092 0.1765 0.037 Uiso calc U . R 1 . .
O O2 0.87446(18) 0.4158(2) 0.27338(12) 0.0533(5) Uani d U . D 1 . .
H H2C 0.828(3) 0.469(4) 0.304(2) 0.08 Uiso d U . D 1 . .
H H2D 0.943(2) 0.348(4) 0.302(2) 0.08 Uiso d U . D 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 111.01(16) ?
C5 N1 H1A . . 107.4(17) ?
C1 N1 H1A . . 110.3(16) ?
C7 N2 H2A . . 120.4(17) ?
C7 N2 H2B . . 120.8(17) ?
H2A N2 H2B . . 119.(2) ?
N1 C1 C2 . . 108.82(16) ?
N1 C1 C6 . . 109.76(16) ?
C2 C1 C6 . . 113.14(17) ?
N1 C1 H1 . . 108.3 ?
C2 C1 H1 . . 108.3 ?
C6 C1 H1 . . 108.3 ?
F1 C2 C3 . . 108.51(16) ?
F1 C2 C1 . . 109.08(15) ?
C3 C2 C1 . . 112.48(18) ?
F1 C2 H2 . . 108.9 ?
C3 C2 H2 . . 108.9 ?
C1 C2 H2 . . 108.9 ?
C2 C3 C4 . . 111.69(17) ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 107.9 ?
C5 C4 C3 . . 109.64(17) ?
C5 C4 H4A . . 109.7 ?
C3 C4 H4A . . 109.7 ?
C5 C4 H4B . . 109.7 ?
C3 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
N1 C5 C4 . . 109.04(17) ?
N1 C5 H5A . . 109.9 ?
C4 C5 H5A . . 109.9 ?
N1 C5 H5B . . 109.9 ?
C4 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
C8 C6 C7 . . 109.23(15) ?
C8 C6 C1 . . 112.89(16) ?
C7 C6 C1 . . 109.54(16) ?
C8 C6 H6 . . 108.4 ?
C7 C6 H6 . . 108.4 ?
C1 C6 H6 . . 108.4 ?
O1 C7 N2 . . 122.97(18) ?
O1 C7 C6 . . 120.74(17) ?
N2 C7 C6 . . 116.27(17) ?
C13 C8 C9 . . 118.48(18) ?
C13 C8 C6 . . 120.41(17) ?
C9 C8 C6 . . 121.09(17) ?
C10 C9 C8 . . 120.52(18) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.44(19) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 119.48(19) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.17(19) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.90(19) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
H2C O2 H2D . . 122.(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C2 . 1.424(2) ?
N1 C5 . 1.473(3) ?
N1 C1 . 1.477(2) ?
N1 H1A . 0.93(3) ?
N2 C7 . 1.329(3) ?
N2 H2A . 0.86(3) ?
N2 H2B . 0.89(3) ?
O1 C7 . 1.236(2) ?
C1 C2 . 1.519(3) ?
C1 C6 . 1.535(3) ?
C1 H1 . 1.0 ?
C2 C3 . 1.511(3) ?
C2 H2 . 1.0 ?
C3 C4 . 1.527(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.520(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C8 . 1.518(3) ?
C6 C7 . 1.533(3) ?
C6 H6 . 1.0 ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.399(3) ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.390(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.391(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
O2 H2C . 0.884(18) ?
O2 H2D . 0.981(18) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 2_655 0.93(3) 2.43(3) 3.208(2) 141.(2) ?
N2 H2A O2 2_645 0.86(3) 2.08(3) 2.943(3) 178.(2) ?
N2 H2B O1 3_656 0.89(3) 2.10(3) 2.957(2) 161.(2) ?
O2 H2C N1 . 0.884(18) 1.989(19) 2.871(2) 174.(3) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -61.7(2) ?
C5 N1 C1 C6 . . . . 174.01(16) ?
N1 C1 C2 F1 . . . . -66.1(2) ?
C6 C1 C2 F1 . . . . 56.2(2) ?
N1 C1 C2 C3 . . . . 54.3(2) ?
C6 C1 C2 C3 . . . . 176.62(15) ?
F1 C2 C3 C4 . . . . 69.8(2) ?
C1 C2 C3 C4 . . . . -51.0(2) ?
C2 C3 C4 C5 . . . . 52.4(2) ?
C1 N1 C5 C4 . . . . 64.9(2) ?
C3 C4 C5 N1 . . . . -58.7(2) ?
N1 C1 C6 C8 . . . . -63.5(2) ?
C2 C1 C6 C8 . . . . 174.78(15) ?
N1 C1 C6 C7 . . . . 174.58(15) ?
C2 C1 C6 C7 . . . . 52.8(2) ?
C8 C6 C7 O1 . . . . -80.3(2) ?
C1 C6 C7 O1 . . . . 43.8(2) ?
C8 C6 C7 N2 . . . . 98.0(2) ?
C1 C6 C7 N2 . . . . -137.89(19) ?
C7 C6 C8 C13 . . . . -110.61(19) ?
C1 C6 C8 C13 . . . . 127.27(19) ?
C7 C6 C8 C9 . . . . 68.0(2) ?
C1 C6 C8 C9 . . . . -54.1(2) ?
C13 C8 C9 C10 . . . . 1.1(3) ?
C6 C8 C9 C10 . . . . -177.55(18) ?
C8 C9 C10 C11 . . . . -0.6(3) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
C10 C11 C12 C13 . . . . 1.2(3) ?
C11 C12 C13 C8 . . . . -0.7(3) ?
C9 C8 C13 C12 . . . . -0.5(3) ?
C6 C8 C13 C12 . . . . 178.20(18) ?
