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#$Date: 2022-11-17 12:17:49 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106140.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_8106140
loop_
_publ_author_name
'Liu, Kuanguan'
'Nie, Jing'
_publ_section_title
;
 Crystal structure of
 bis(4-dimethylamino-pyridin-1-ium)tetrafluorosuccinate, C18H22F4N4O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              321
_journal_page_last               323
_journal_paper_doi               10.1515/ncrs-2017-0318
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H22 F4 N4 O4'
_chemical_formula_sum            'C18 H22 F4 N4 O4'
_chemical_formula_weight         434.39
_chemical_name_common
;
4-dimethylamino-pyridinium tetrafluorosuccinate
;
_chemical_name_systematic
;
di(4-dimethylamino-pyridinium) tetrafluorosuccinate
;
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.240(4)
_cell_angle_beta                 72.215(4)
_cell_angle_gamma                71.531(4)
_cell_formula_units_Z            1
_cell_length_a                   7.3295(9)
_cell_length_b                   8.6026(9)
_cell_length_c                   8.8041(11)
_cell_measurement_reflns_used    1747
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.38
_cell_volume                     496.61(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7483
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.453
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.992
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.328
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1022
_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)+(0.0117P)²+0.7111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1215
_reflns_number_total             1723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0318_suppl.cif
_cod_data_source_block           P
_cod_database_code               8106140
_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   0.957
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71241   7.330   8.603   8.804   77.240   72.215   71.531
;
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
C11 C 0.1463(6) 0.8505(5) 0.8319(5) 0.0405(10) Uani 1 1 d . . . . .
O1 O 0.1108(5) 0.9107(4) 0.6975(3) 0.0594(10) Uani 1 1 d . . . . .
O2 O 0.2073(5) 0.7060(4) 0.8861(4) 0.0584(9) Uani 1 1 d . . . . .
C12 C 0.1043(6) 0.9814(5) 0.9442(5) 0.0378(10) Uani 1 1 d . . . . .
F1 F 0.2361(3) 0.9309(3) 1.0387(3) 0.0492(7) Uani 1 1 d . . . . .
F2 F 0.1335(4) 1.1285(3) 0.8572(3) 0.0501(7) Uani 1 1 d . . . . .
N1 N 0.2027(5) 0.6524(4) 0.5333(4) 0.0460(9) Uani 1 1 d . . . . .
H1N H 0.1775 0.7293 0.5906 0.069 Uiso 1 1 calc R U . . .
C1 C 0.2521(6) 0.4932(6) 0.5980(5) 0.0479(12) Uani 1 1 d . . . . .
H1 H 0.2608 0.4675 0.7043 0.058 Uiso 1 1 calc R U . . .
C2 C 0.2897(6) 0.3689(5) 0.5117(5) 0.0435(11) Uani 1 1 d . . . . .
H2 H 0.3227 0.2595 0.5594 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2789(6) 0.4052(5) 0.3492(5) 0.0336(9) Uani 1 1 d . . . . .
C4 C 0.2315(6) 0.5755(5) 0.2850(5) 0.0386(10) Uani 1 1 d . . . . .
H4 H 0.2273 0.6067 0.1778 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1924(6) 0.6921(5) 0.3798(5) 0.0428(11) Uani 1 1 d . . . . .
H5 H 0.1574 0.8031 0.3371 0.051 Uiso 1 1 calc R U . . .
N2 N 0.3065(5) 0.2874(4) 0.2611(4) 0.0373(9) Uani 1 1 d . . . . .
C6 C 0.3515(8) 0.1125(5) 0.3287(6) 0.0572(13) Uani 1 1 d . . . . .
H6A H 0.4778 0.0801 0.3544 0.086 Uiso 1 1 calc R U . . .
H6B H 0.3566 0.0471 0.2514 0.086 Uiso 1 1 calc R U . . .
H6C H 0.2498 0.0953 0.4247 0.086 Uiso 1 1 calc R U . . .
C7 C 0.2959(8) 0.3278(6) 0.0937(5) 0.0537(13) Uani 1 1 d . . . . .
H7A H 0.1648 0.3947 0.0884 0.081 Uiso 1 1 calc R U . . .
H7B H 0.3243 0.2276 0.0497 0.081 Uiso 1 1 calc R U . . .
H7C H 0.3915 0.3877 0.0329 0.081 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O2 C11 O1 129.3(4) . .
O2 C11 C12 116.4(4) . .
O1 C11 C12 114.2(4) . .
F2 C12 F1 105.1(3) . .
F2 C12 C12 107.4(4) . 2_577
F1 C12 C12 107.4(4) . 2_577
F2 C12 C11 111.3(3) . .
F1 C12 C11 110.5(3) . .
C12 C12 C11 114.6(4) 2_577 .
C5 N1 C1 120.2(4) . .
C5 N1 H1N 119.9 . .
C1 N1 H1N 119.9 . .
N1 C1 C2 121.4(4) . .
N1 C1 H1 119.3 . .
C2 C1 H1 119.3 . .
C1 C2 C3 120.3(4) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
N2 C3 C2 122.6(4) . .
N2 C3 C4 121.3(4) . .
C2 C3 C4 116.1(4) . .
C5 C4 C3 120.0(4) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
N1 C5 C4 122.0(4) . .
N1 C5 H5 119.0 . .
C4 C5 H5 119.0 . .
C3 N2 C7 121.5(3) . .
C3 N2 C6 121.1(3) . .
C7 N2 C6 117.3(3) . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 H7A 109.5 . .
N2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 O2 1.221(5) .
C11 O1 1.252(5) .
C11 C12 1.558(6) .
C12 F2 1.370(4) .
C12 F1 1.371(4) .
C12 C12 1.522(8) 2_577
N1 C5 1.338(5) .
N1 C1 1.341(5) .
N1 H1N 0.8600 .
C1 C2 1.357(6) .
C1 H1 0.9300 .
C2 C3 1.416(5) .
C2 H2 0.9300 .
C3 N2 1.338(5) .
C3 C4 1.420(5) .
C4 C5 1.351(5) .
C4 H4 0.9300 .
C5 H5 0.9300 .
N2 C7 1.458(5) .
N2 C6 1.462(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
