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#$Date: 2020-10-03 00:23:57 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518111.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_4518111
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            'C12 H13 F4 N'
_chemical_formula_weight         247.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6845(4)
_cell_length_b                   6.2599(2)
_cell_length_c                   21.2252(5)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6586
_cell_measurement_theta_min      4.1657
_cell_volume                     2216.83(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  0.0443
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14196
_diffrn_reflns_theta_full        66.65
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         4.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.174
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.78
_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    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1962
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0414
_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)+(0.0713P)²+0.7190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                1671
_reflns_number_total             1962
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c03278_si_002.cif
_cod_data_source_block           glo9642
_cod_database_code               4518111
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
N N1 0.30474(9) 0.8930(3) 0.15372(6) 0.0279(4) Uani d . . . 1.0 . .
H H1 0.2548(15) 0.829(4) 0.1612(10) 0.041(6) Uiso d . . . 1.0 . .
C C2 0.36997(10) 0.7477(3) 0.17114(8) 0.0223(4) Uani d . . . 1.0 . .
H H2 0.3688 0.6218 0.1421 0.027 Uiso calc U . R 1.0 . .
C C3 0.44980(10) 0.8644(3) 0.16256(8) 0.0262(4) Uani d . . . 1.0 . .
H H3A 0.4519 0.9894 0.1911 0.031 Uiso calc U . R 1.0 . .
H H3B 0.4945 0.7676 0.1737 0.031 Uiso calc U . R 1.0 . .
C C4 0.45939(11) 0.9389(3) 0.09434(8) 0.0305(4) Uani d . . . 1.0 . .
H H4A 0.5081 1.0284 0.0907 0.037 Uiso calc U . R 1.0 . .
H H4B 0.4663 0.8131 0.0666 0.037 Uiso calc U . R 1.0 . .
C C5 0.38744(12) 1.0657(3) 0.07294(8) 0.0315(4) Uani d . . D 1.0 . .
H H5 0.3914 1.092 0.0266 0.038 Uiso calc U P R 0.76(3) A 1
H H5A 0.3914 1.088 0.0264 0.038 Uiso calc U P R 0.24(3) A 2
F F1 0.3817(5) 1.2642(5) 0.10488(19) 0.0316(10) Uani d U P D 0.76(3) A 1
F F1A 0.413(2) 1.262(2) 0.1047(7) 0.052(4) Uani d U P D 0.24(3) A 2
C C6 0.31034(11) 0.9507(3) 0.08697(8) 0.0312(4) Uani d . . . 1.0 . .
H H6A 0.2645 1.0435 0.0756 0.037 Uiso calc U . R 1.0 . .
H H6B 0.3072 0.8197 0.061 0.037 Uiso calc U . R 1.0 . .
C C7 0.36220(9) 0.6687(3) 0.23812(7) 0.0213(4) Uani d . . . 1.0 . .
C C8 0.33134(10) 0.7961(3) 0.28602(7) 0.0228(4) Uani d . . . 1.0 . .
H H8 0.3107 0.9337 0.2764 0.027 Uiso calc U . R 1.0 . .
C C9 0.33057(9) 0.7235(3) 0.34792(8) 0.0231(4) Uani d . . . 1.0 . .
H H9 0.3096 0.8116 0.3804 0.028 Uiso calc U . R 1.0 . .
C C10 0.36040(9) 0.5230(3) 0.36221(8) 0.0226(4) Uani d . . . 1.0 . .
C C11 0.39061(10) 0.3919(3) 0.31468(8) 0.0244(4) Uani d . . . 1.0 . .
H H11 0.4107 0.2537 0.3243 0.029 Uiso calc U . R 1.0 . .
C C12 0.39093(10) 0.4663(3) 0.25303(8) 0.0236(4) Uani d . . . 1.0 . .
H H12 0.4112 0.3773 0.2204 0.028 Uiso calc U . R 1.0 . .
C C13 0.36292(10) 0.4468(3) 0.42904(8) 0.0271(4) Uani d . . . 1.0 . .
F F2 0.43225(8) 0.4911(2) 0.45752(5) 0.0504(4) Uani d . . . 1.0 . .
F F3 0.35427(7) 0.23427(18) 0.43380(5) 0.0388(3) Uani d . . . 1.0 . .
F F4 0.30519(8) 0.5319(2) 0.46433(5) 0.0511(4) Uani d . . . 1.0 . .
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'
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
C6 N1 C2 . . 110.46(13) ?
C6 N1 H1 . . 109.0(13) ?
C2 N1 H1 . . 110.7(14) ?
N1 C2 C7 . . 112.13(13) ?
N1 C2 C3 . . 108.66(14) ?
C7 C2 C3 . . 110.07(13) ?
N1 C2 H2 . . 108.6 ?
C7 C2 H2 . . 108.6 ?
C3 C2 H2 . . 108.6 ?
C4 C3 C2 . . 110.45(14) ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3B . . 109.6 ?
C2 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 111.22(15) ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
F1 C5 C6 . . 105.5(3) ?
F1A C5 C6 . . 123.9(13) ?
F1 C5 C4 . . 111.7(3) ?
F1A C5 C4 . . 94.2(14) ?
C6 C5 C4 . . 111.66(15) ?
F1 C5 H5 . . 109.3 ?
C6 C5 H5 . . 109.3 ?
C4 C5 H5 . . 109.3 ?
F1A C5 H5A . . 108.6 ?
C6 C5 H5A . . 108.6 ?
C4 C5 H5A . . 108.6 ?
N1 C6 C5 . . 111.35(15) ?
N1 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
N1 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C12 C7 C8 . . 118.92(15) ?
C12 C7 C2 . . 118.86(14) ?
C8 C7 C2 . . 122.12(15) ?
C9 C8 C7 . . 120.43(16) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.02(15) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 120.33(16) ?
C9 C10 C13 . . 120.45(16) ?
C11 C10 C13 . . 119.19(16) ?
C12 C11 C10 . . 119.05(16) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C7 . . 121.23(15) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
F4 C13 F2 . . 106.79(15) ?
F4 C13 F3 . . 106.06(15) ?
F2 C13 F3 . . 105.38(15) ?
F4 C13 C10 . . 112.66(15) ?
F2 C13 C10 . . 112.79(14) ?
F3 C13 C10 . . 112.60(15) ?
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
N1 C6 . 1.465(2) ?
N1 C2 . 1.466(2) ?
N1 H1 . 0.94(2) ?
C2 C7 . 1.511(2) ?
C2 C3 . 1.530(2) ?
C2 H2 . 1.0 ?
C3 C4 . 1.530(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.509(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 F1 . 1.419(4) ?
C5 F1A . 1.463(15) ?
C5 C6 . 1.504(3) ?
C5 H5 . 1.0 ?
C5 H5A . 1.0 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C12 . 1.391(2) ?
C7 C8 . 1.391(2) ?
C8 C9 . 1.390(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.395(2) ?
C10 C13 . 1.497(2) ?
C11 C12 . 1.389(2) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 F4 . 1.331(2) ?
C13 F2 . 1.334(2) ?
C13 F3 . 1.342(2) ?
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 H1 F1 8_655 0.94(2) 2.60(2) 3.377(8) 140.0(17) ?
C2 H2 F1 1_545 1.0 2.38 3.343(3) 160.5 ?
C2 H2 F1A 1_545 1.0 2.5 3.427(16) 154.2 ?
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
C6 N1 C2 C7 . . . . -174.91(15) ?
C6 N1 C2 C3 . . . . 63.20(18) ?
N1 C2 C3 C4 . . . . -58.63(18) ?
C7 C2 C3 C4 . . . . 178.23(14) ?
C2 C3 C4 C5 . . . . 52.5(2) ?
C3 C4 C5 F1 . . . . 67.9(3) ?
C3 C4 C5 F1A . . . . 79.1(9) ?
C3 C4 C5 C6 . . . . -50.0(2) ?
C2 N1 C6 C5 . . . . -61.6(2) ?
F1 C5 C6 N1 . . . . -67.2(3) ?
F1A C5 C6 N1 . . . . -56.9(13) ?
C4 C5 C6 N1 . . . . 54.4(2) ?
N1 C2 C7 C12 . . . . 149.17(15) ?
C3 C2 C7 C12 . . . . -89.75(18) ?
N1 C2 C7 C8 . . . . -34.5(2) ?
C3 C2 C7 C8 . . . . 86.60(18) ?
C12 C7 C8 C9 . . . . 1.1(2) ?
C2 C7 C8 C9 . . . . -175.26(15) ?
C7 C8 C9 C10 . . . . -0.2(2) ?
C8 C9 C10 C11 . . . . -0.7(2) ?
C8 C9 C10 C13 . . . . 177.51(15) ?
C9 C10 C11 C12 . . . . 0.6(2) ?
C13 C10 C11 C12 . . . . -177.62(15) ?
C10 C11 C12 C7 . . . . 0.4(2) ?
C8 C7 C12 C11 . . . . -1.2(2) ?
C2 C7 C12 C11 . . . . 175.29(15) ?
C9 C10 C13 F4 . . . . 29.1(2) ?
C11 C10 C13 F4 . . . . -152.71(16) ?
C9 C10 C13 F2 . . . . -91.89(19) ?
C11 C10 C13 F2 . . . . 86.3(2) ?
C9 C10 C13 F3 . . . . 149.00(16) ?
C11 C10 C13 F3 . . . . -32.8(2) ?
