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#$Date: 2025-01-11 04:21:54 +0200 (Sat, 11 Jan 2025) $
#$Revision: 297283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312738.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312738
loop_
_publ_author_name
'Hollenwäger, Dirk'
'Leitz, Dominik'
'Bockmair, Valentin'
'Kornath, Andreas J.'
_publ_section_title
;
 Monoprotonated species of 2-aminomalonyl difluoride,
 [C₃H₄F₂NO₂][H₂F₃].
;
_journal_coeditor_code           OJ3024
_journal_issue                   2
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624012452
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C3 H3 F2 N O2 +, H2 F3 -'
_chemical_formula_moiety         'C3 H3 F2 N O2 +, H2 F3 -'
_chemical_formula_sum            'C3 H6 F5 N O2'
_chemical_formula_weight         183.09
_chemical_name_systematic
;
1,3-Difluoro-1,3-dioxopropan-2-aminium dihydrogen trifluoride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5736(2)
_cell_length_b                   9.2154(4)
_cell_length_c                   12.7952(7)
_cell_measurement_reflns_used    2040
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      31.1830
_cell_measurement_theta_min      2.7220
_cell_volume                     657.20(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      102(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7118
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.302
_diffrn_reflns_theta_min         2.724
_diffrn_source_current           40
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.181
_refine_ls_abs_structure_details
;
Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0338
_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)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                1930
_reflns_number_total             2187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3024.cif
_cod_data_source_block           I
_cod_database_code               2312738
_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   0.926
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.0476(2) 0.32000(12) 0.02215(9) 0.0243(3) Uani d 1 . .
F F2 0.4306(2) 0.50434(12) 0.05212(8) 0.0244(3) Uani d 1 . .
O O2 0.4408(2) 0.58347(13) 0.21402(10) 0.0202(3) Uani d 1 . .
O O1 -0.1665(2) 0.31969(15) 0.16660(11) 0.0210(3) Uani d 1 . .
N N1 0.2218(3) 0.34495(18) 0.29301(12) 0.0171(3) Uani d 1 . .
C C1 0.0210(3) 0.33015(19) 0.12529(14) 0.0178(3) Uani d 1 . .
C C2 0.3829(3) 0.49451(19) 0.15364(13) 0.0160(3) Uani d 1 . .
C C3 0.2606(3) 0.35165(19) 0.17959(14) 0.0148(3) Uani d 1 . .
H H1 0.154(4) 0.257(3) 0.3148(19) 0.025(6) Uiso d 1 . .
H H2 0.126(4) 0.414(2) 0.3121(17) 0.020(5) Uiso d 1 . .
H H4 0.362(4) 0.275(2) 0.1562(15) 0.012(5) Uiso d 1 . .
H H3 0.355(4) 0.363(3) 0.331(2) 0.037(7) Uiso d 1 . .
F F4 0.88392(19) 0.54834(12) 0.34615(9) 0.0225(2) Uani d 1 . .
F F5 0.53500(19) 0.38358(12) 0.59645(9) 0.0221(2) Uani d 1 . .
F F3 0.59728(18) 0.39321(12) 0.41590(9) 0.0239(3) Uani d 1 . .
H H5 0.784(6) 0.482(4) 0.378(3) 0.071(11) Uiso d 1 . .
H H6 0.562(5) 0.385(4) 0.524(3) 0.070(9) Uiso 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 H1 . . 112.9(15) ?
C3 N1 H2 . . 109.8(14) ?
H1 N1 H2 . . 107.6(19) ?
C3 N1 H3 . . 113.6(15) ?
H1 N1 H3 . . 109(2) ?
H2 N1 H3 . . 103(2) ?
O1 C1 F1 . . 122.64(16) ?
O1 C1 C3 . . 125.94(17) ?
F1 C1 C3 . . 111.40(14) ?
O2 C2 F2 . . 122.80(16) ?
O2 C2 C3 . . 125.85(16) ?
F2 C2 C3 . . 111.25(14) ?
N1 C3 C1 . . 108.51(14) ?
N1 C3 C2 . . 108.57(14) ?
C1 C3 C2 . . 114.07(14) ?
N1 C3 H4 . . 111.5(12) ?
C1 C3 H4 . . 106.3(12) ?
C2 C3 H4 . . 107.9(12) ?
H5 F3 H6 . . 118.6(19) ?
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 C1 . 1.331(2) ?
F2 C2 . 1.329(2) ?
O2 C2 . 1.172(2) ?
O1 C1 . 1.175(2) ?
N1 C3 . 1.469(2) ?
N1 H1 . 0.94(2) ?
N1 H2 . 0.87(2) ?
N1 H3 . 0.90(3) ?
C1 C3 . 1.518(2) ?
C2 C3 . 1.519(2) ?
C3 H4 . 0.95(2) ?
F4 H5 . 0.92(4) ?
F5 H6 . 0.94(3) ?
F3 H5 . 1.41(4) ?
F3 H6 . 1.40(3) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
C1 F4 2.676(2)
C1 F5 2.682(2)
C2 F5 2.688(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 F5 4_456 0.94(2) 1.84(2) 2.7422(19) 159(2) yes
N1 H2 F4 1_455 0.87(2) 1.88(2) 2.7426(19) 172(2) yes
N1 H3 F3 . 0.90(3) 1.75(3) 2.6551(19) 174(2) yes
F4 H5 F3 . 0.92(4) 1.41(4) 2.3221(15) 170(3) yes
F5 H6 F3 . 0.94(3) 1.40(3) 2.3378(16) 177(3) yes
N1 H1 F5 4_456 0.94(2) 1.84(2) 2.7422(19) 159(2) yes
N1 H2 F4 1_455 0.87(2) 1.88(2) 2.7426(19) 172(2) yes
N1 H3 F3 . 0.90(3) 1.75(3) 2.6551(19) 174(2) yes
F4 H5 F3 . 0.92(4) 1.41(4) 2.3221(15) 170(3) yes
F5 H6 F3 . 0.94(3) 1.40(3) 2.3378(16) 177(3) yes
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
O1 C1 C3 N1 . . . . 4.7(3) ?
F1 C1 C3 N1 . . . . -173.50(14) ?
O1 C1 C3 C2 . . . . -116.4(2) ?
F1 C1 C3 C2 . . . . 65.34(19) ?
O2 C2 C3 N1 . . . . 1.3(2) ?
F2 C2 C3 N1 . . . . 177.71(13) ?
O2 C2 C3 C1 . . . . 122.37(19) ?
F2 C2 C3 C1 . . . . -61.17(18) ?
