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#$Date: 2022-09-21 12:23:46 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105821.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_8105821
loop_
_publ_author_name
'Wardell, James L.'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of
 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium
 trifluoroacetate, [C17H17F6N2O][C2F3O2]
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              687
_journal_page_last               689
_journal_paper_doi               10.1515/ncrs-2019-0037
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C17 H17 F6 N2 O1, C2 F3 O2'
_chemical_formula_sum            'C19 H17 F9 N2 O3'
_chemical_formula_weight         492.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                105.6170(10)
_cell_angle_beta                 102.1890(10)
_cell_angle_gamma                106.0750(10)
_cell_formula_units_Z            2
_cell_length_a                   7.98730(10)
_cell_length_b                   11.0534(2)
_cell_length_c                   13.2380(3)
_cell_measurement_reflns_used    116778
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1028.76(3)
_computing_cell_refinement
;
COLLECT [2] & DENZO [3] 
;
_computing_data_collection       'COLLECT [2]'
_computing_data_reduction
;
COLLECT [2] & DENZO [3] 
;
_computing_molecular_graphics
;
ORTEP-3 for Windows [6]
;
_computing_publication_material  'SHELXL2014/7 [5]'
_computing_structure_refinement  'SHELXL2014/7 [5]'
_computing_structure_solution    'SHELXS [4]'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on κ-goniostat
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21617
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.067
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       slab
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0403
_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)+(0.0551P)²+0.5713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4151
_reflns_number_total             4704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0037_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8105821
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.02951(15) 0.37548(13) 0.38214(8) 0.0493(3) Uani 1 1 d . . . . .
F2 F 0.24872(13) 0.52419(9) 0.52189(9) 0.0385(2) Uani 1 1 d . . . . .
F3 F 0.07811(13) 0.35051(10) 0.53895(9) 0.0361(2) Uani 1 1 d . . . . .
F4 F 0.68301(14) 0.41825(10) 0.73814(8) 0.0408(3) Uani 1 1 d . . . . .
F5 F 0.46179(15) 0.24409(12) 0.72416(8) 0.0423(3) Uani 1 1 d . . . . .
F6 F 0.74099(17) 0.25665(13) 0.78058(8) 0.0521(3) Uani 1 1 d . . . . .
O1 O 0.27515(13) 0.17013(11) 0.11193(8) 0.0239(2) Uani 1 1 d D . . . .
H1O H 0.1761(18) 0.1277(18) 0.1191(16) 0.036 Uiso 1 1 d D U . . .
N1 N 0.39162(15) 0.30406(11) 0.52565(9) 0.0181(2) Uani 1 1 d . . . . .
N2 N 0.62889(15) 0.20936(11) 0.08180(9) 0.0185(2) Uani 1 1 d D . . . .
H1N H 0.646(2) 0.1342(12) 0.0828(14) 0.022 Uiso 1 1 d D U . . .
H2N H 0.5280(16) 0.1840(16) 0.0269(11) 0.022 Uiso 1 1 d D U . . .
C1 C 0.28884(17) 0.31996(12) 0.44213(10) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.29300(17) 0.27831(13) 0.33286(10) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.2188 0.2974 0.2774 0.021 Uiso 1 1 calc R U . . .
C3 C 0.40643(17) 0.20954(12) 0.30800(10) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.51298(17) 0.18144(12) 0.39366(10) 0.0158(2) Uani 1 1 d . . . . .
C5 C 0.62722(18) 0.10427(13) 0.37625(11) 0.0196(3) Uani 1 1 d . . . . .
H5 H 0.6313 0.0656 0.3039 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7309(2) 0.08547(14) 0.46279(12) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.8045 0.0321 0.4498 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7302(2) 0.14432(15) 0.57128(12) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.8063 0.1329 0.6309 0.030 Uiso 1 1 calc R U . . .
C8 C 0.62047(19) 0.21783(14) 0.59121(11) 0.0217(3) Uani 1 1 d . . . . .
C9 C 0.50491(17) 0.23564(12) 0.50262(10) 0.0168(2) Uani 1 1 d . . . . .
C10 C 0.16075(18) 0.39259(13) 0.47126(11) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.6245(2) 0.28366(17) 0.70762(12) 0.0311(3) Uani 1 1 d . . . . .
C12 C 0.42225(17) 0.16880(13) 0.19225(10) 0.0175(2) Uani 1 1 d . . . . .
H12 H 0.4292 0.0768 0.1715 0.021 Uiso 1 1 calc R U . . .
C13 C 0.59788(17) 0.26909(12) 0.18944(10) 0.0170(2) Uani 1 1 d . . . . .
H13 H 0.7034 0.2787 0.2510 0.020 Uiso 1 1 calc R U . . .
C14 C 0.7893(2) 0.29819(15) 0.06226(13) 0.0274(3) Uani 1 1 d . . . . .
H14A H 0.7937 0.2554 -0.0127 0.033 Uiso 1 1 calc R U . . .
H14B H 0.9041 0.3092 0.1161 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7754(2) 0.43488(16) 0.07357(14) 0.0326(3) Uani 1 1 d . . . . .
H15A H 0.6672 0.4251 0.0150 0.039 Uiso 1 1 calc R U . . .
H15B H 0.8859 0.4935 0.0648 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7578(2) 0.49892(15) 0.18635(13) 0.0314(3) Uani 1 1 d . . . . .
H16A H 0.7470 0.5876 0.1929 0.038 Uiso 1 1 calc R U . . .
H16B H 0.8686 0.5128 0.2449 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5886(2) 0.40794(13) 0.20090(12) 0.0242(3) Uani 1 1 d . . . . .
H17A H 0.5790 0.4497 0.2746 0.029 Uiso 1 1 calc R U . . .
H17B H 0.4776 0.3988 0.1448 0.029 Uiso 1 1 calc R U . . .
F7 F -0.08877(16) -0.11720(14) 0.25094(9) 0.0527(3) Uani 1 1 d . . . . .
F8 F -0.2559(2) -0.25218(11) 0.08871(10) 0.0584(4) Uani 1 1 d . . . . .
F9 F 0.0247(2) -0.13334(18) 0.11646(14) 0.0802(5) Uani 1 1 d . . . . .
O2 O -0.06241(14) 0.08467(11) 0.13035(10) 0.0345(3) Uani 1 1 d . . . . .
O3 O -0.35082(13) -0.03455(10) 0.10914(8) 0.0235(2) Uani 1 1 d . . . . .
C18 C -0.18437(19) -0.01618(14) 0.12451(10) 0.0213(3) Uani 1 1 d . . . . .
C19 C -0.1253(3) -0.13127(19) 0.14389(14) 0.0367(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O1 H1O 108.8(14) . .
C1 N1 C9 116.78(11) . .
C14 N2 C13 114.46(10) . .
C14 N2 H1N 109.6(11) . .
C13 N2 H1N 106.2(11) . .
C14 N2 H2N 111.2(11) . .
C13 N2 H2N 109.9(11) . .
H1N N2 H2N 104.9(15) . .
N1 C1 C2 125.51(12) . .
N1 C1 C10 114.81(11) . .
C2 C1 C10 119.66(11) . .
C3 C2 C1 118.54(12) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C2 C3 C4 118.65(11) . .
C2 C3 C12 120.24(11) . .
C4 C3 C12 121.07(11) . .
C5 C4 C3 123.59(11) . .
C5 C4 C9 118.86(11) . .
C3 C4 C9 117.54(11) . .
C6 C5 C4 120.51(12) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 120.79(12) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C8 C7 C6 120.42(13) . .
C8 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C7 C8 C9 120.53(12) . .
C7 C8 C11 120.07(12) . .
C9 C8 C11 119.38(12) . .
N1 C9 C8 118.51(11) . .
N1 C9 C4 122.74(11) . .
C8 C9 C4 118.75(11) . .
F3 C10 F2 106.12(11) . .
F3 C10 F1 106.95(12) . .
F2 C10 F1 107.20(12) . .
F3 C10 C1 112.36(11) . .
F2 C10 C1 112.00(11) . .
F1 C10 C1 111.83(11) . .
F5 C11 F4 107.09(13) . .
F5 C11 F6 106.40(13) . .
F4 C11 F6 105.79(13) . .
F5 C11 C8 113.51(13) . .
F4 C11 C8 112.11(12) . .
F6 C11 C8 111.45(12) . .
O1 C12 C3 113.37(10) . .
O1 C12 C13 106.34(10) . .
C3 C12 C13 109.40(10) . .
O1 C12 H12 109.2 . .
C3 C12 H12 109.2 . .
C13 C12 H12 109.2 . .
N2 C13 C17 109.91(10) . .
N2 C13 C12 107.34(10) . .
C17 C13 C12 113.63(11) . .
N2 C13 H13 108.6 . .
C17 C13 H13 108.6 . .
C12 C13 H13 108.6 . .
N2 C14 C15 111.01(12) . .
N2 C14 H14A 109.4 . .
C15 C14 H14A 109.4 . .
N2 C14 H14B 109.4 . .
C15 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C14 C15 C16 110.08(12) . .
C14 C15 H15A 109.6 . .
C16 C15 H15A 109.6 . .
C14 C15 H15B 109.6 . .
C16 C15 H15B 109.6 . .
H15A C15 H15B 108.2 . .
C15 C16 C17 109.83(12) . .
C15 C16 H16A 109.7 . .
C17 C16 H16A 109.7 . .
C15 C16 H16B 109.7 . .
C17 C16 H16B 109.7 . .
H16A C16 H16B 108.2 . .
C13 C17 C16 111.47(12) . .
C13 C17 H17A 109.3 . .
C16 C17 H17A 109.3 . .
C13 C17 H17B 109.3 . .
C16 C17 H17B 109.3 . .
H17A C17 H17B 108.0 . .
O2 C18 O3 127.74(13) . .
O2 C18 C19 116.74(13) . .
O3 C18 C19 115.45(13) . .
F9 C19 F8 107.97(16) . .
F9 C19 F7 107.32(15) . .
F8 C19 F7 106.09(14) . .
F9 C19 C18 112.30(14) . .
F8 C19 C18 112.88(13) . .
F7 C19 C18 109.95(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C10 1.3320(16) .
F2 C10 1.3301(16) .
F3 C10 1.3264(16) .
F4 C11 1.344(2) .
F5 C11 1.336(2) .
F6 C11 1.3478(17) .
O1 C12 1.4148(15) .
O1 H1O 0.840(9) .
N1 C1 1.3147(17) .
N1 C9 1.3620(16) .
N2 C14 1.5009(17) .
N2 C13 1.5037(15) .
N2 H1N 0.881(9) .
N2 H2N 0.880(9) .
C1 C2 1.4056(18) .
C1 C10 1.5149(17) .
C2 C3 1.3710(17) .
C2 H2 0.9500 .
C3 C4 1.4266(17) .
C3 C12 1.5194(17) .
C4 C5 1.4238(17) .
C4 C9 1.4280(17) .
C5 C6 1.3655(19) .
C5 H5 0.9500 .
C6 C7 1.410(2) .
C6 H6 0.9500 .
C7 C8 1.3690(19) .
C7 H7 0.9500 .
C8 C9 1.4262(18) .
C8 C11 1.5057(19) .
C12 C13 1.5430(17) .
C12 H12 1.0000 .
C13 C17 1.5252(18) .
C13 H13 1.0000 .
C14 C15 1.515(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.525(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.528(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
F7 C19 1.3413(19) .
F8 C19 1.337(2) .
F9 C19 1.328(2) .
O2 C18 1.2320(18) .
O3 C18 1.2507(17) .
C18 C19 1.537(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 N1 C1 C2 -3.36(19) . . . .
C9 N1 C1 C10 178.07(11) . . . .
N1 C1 C2 C3 3.2(2) . . . .
C10 C1 C2 C3 -178.24(11) . . . .
C1 C2 C3 C4 0.98(18) . . . .
C1 C2 C3 C12 -176.93(11) . . . .
C2 C3 C4 C5 176.25(12) . . . .
C12 C3 C4 C5 -5.86(18) . . . .
C2 C3 C4 C9 -4.50(17) . . . .
C12 C3 C4 C9 173.39(11) . . . .
C3 C4 C5 C6 177.52(12) . . . .
C9 C4 C5 C6 -1.71(19) . . . .
C4 C5 C6 C7 -1.4(2) . . . .
C5 C6 C7 C8 2.2(2) . . . .
C6 C7 C8 C9 0.2(2) . . . .
C6 C7 C8 C11 -178.23(14) . . . .
C1 N1 C9 C8 179.16(11) . . . .
C1 N1 C9 C4 -0.68(18) . . . .
C7 C8 C9 N1 176.89(12) . . . .
C11 C8 C9 N1 -4.66(19) . . . .
C7 C8 C9 C4 -3.3(2) . . . .
C11 C8 C9 C4 175.19(12) . . . .
C5 C4 C9 N1 -176.18(11) . . . .
C3 C4 C9 N1 4.54(18) . . . .
C5 C4 C9 C8 3.98(18) . . . .
C3 C4 C9 C8 -175.31(11) . . . .
N1 C1 C10 F3 -43.48(16) . . . .
C2 C1 C10 F3 137.86(12) . . . .
N1 C1 C10 F2 75.87(15) . . . .
C2 C1 C10 F2 -102.80(14) . . . .
N1 C1 C10 F1 -163.77(12) . . . .
C2 C1 C10 F1 17.57(18) . . . .
C7 C8 C11 F5 -121.48(15) . . . .
C9 C8 C11 F5 60.06(18) . . . .
C7 C8 C11 F4 117.00(15) . . . .
C9 C8 C11 F4 -61.46(18) . . . .
C7 C8 C11 F6 -1.4(2) . . . .
C9 C8 C11 F6 -179.83(13) . . . .
C2 C3 C12 O1 -18.51(17) . . . .
C4 C3 C12 O1 163.63(11) . . . .
C2 C3 C12 C13 99.99(13) . . . .
C4 C3 C12 C13 -77.87(14) . . . .
C14 N2 C13 C17 52.48(15) . . . .
C14 N2 C13 C12 176.51(11) . . . .
O1 C12 C13 N2 -69.08(12) . . . .
C3 C12 C13 N2 168.14(10) . . . .
O1 C12 C13 C17 52.65(13) . . . .
C3 C12 C13 C17 -70.13(14) . . . .
C13 N2 C14 C15 -54.08(16) . . . .
N2 C14 C15 C16 55.97(17) . . . .
C14 C15 C16 C17 -58.60(18) . . . .
N2 C13 C17 C16 -54.15(15) . . . .
C12 C13 C17 C16 -174.44(11) . . . .
C15 C16 C17 C13 58.36(17) . . . .
O2 C18 C19 F9 -27.9(2) . . . .
O3 C18 C19 F9 154.92(16) . . . .
O2 C18 C19 F8 -150.29(13) . . . .
O3 C18 C19 F8 32.58(18) . . . .
O2 C18 C19 F7 91.47(17) . . . .
O3 C18 C19 F7 -85.66(17) . . . .
