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#$Date: 2024-08-07 01:02:50 +0300 (Wed, 07 Aug 2024) $
#$Revision: 293982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312524.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_2312524
loop_
_publ_author_name
'Hollenwäger, Dirk'
'Nitzer, Alexander'
'Bockmair, Valentin'
'Kornath, Andreas J.'
_publ_section_title
;
 The crystal structure of the ammonium salt of 2-aminomalonic acid.
;
_journal_coeditor_code           WV3014
_journal_issue                   'Pt 7'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              291
_journal_page_last               296
_journal_paper_doi               10.1107/S2053229624005576
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'N H4 +, C3 H4 N O4 -'
_chemical_formula_moiety         'H4 N +, C3 H4 N O4 -'
_chemical_formula_sum            'C3 H8 N2 O4'
_chemical_formula_weight         136.11
_chemical_name_common
;
Ammonium 2-amminomalonate
;
_chemical_name_systematic
;
Ammonium 2-azaniumylpropanedioate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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            8
_cell_length_a                   9.9714(4)
_cell_length_b                   9.8671(3)
_cell_length_c                   11.1884(4)
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      32.2920
_cell_measurement_theta_min      2.1190
_cell_volume                     1100.81(7)
_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 (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         3.428
_diffrn_source_current           40
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.726
_exptl_crystal_size_mid          0.597
_exptl_crystal_size_min          0.509
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0386
_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)+(0.0446P)²+0.9120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                1391
_reflns_number_total             1483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wv3014.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2312524.cif.'
_cod_database_code               2312524
_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   0.898
_shelx_estimated_absorpt_t_max   0.927
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'
'-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
N N2 0.50374(12) 0.23766(12) 0.51186(11) 0.0124(2) Uani d 1 . .
H H4 0.515(2) 0.233(2) 0.438(2) 0.027(5) Uiso d 1 . .
H H3 0.461(2) 0.167(2) 0.5344(19) 0.024(5) Uiso d 1 . .
H H5 0.456(2) 0.308(2) 0.534(2) 0.026(5) Uiso d 1 . .
H H6 0.584(2) 0.238(2) 0.545(2) 0.024(5) Uiso d 1 . .
O O3 0.64253(10) 0.50248(10) 0.92457(9) 0.0151(2) Uani d 1 . .
O O4 0.86733(10) 0.49144(10) 0.93630(9) 0.0145(2) Uani d 1 . .
O O2 0.93388(10) 0.29895(10) 0.74002(9) 0.0136(2) Uani d 1 . .
O O1 0.74231(10) 0.26216(10) 0.64267(10) 0.0165(2) Uani d 1 . .
C C3 0.75713(13) 0.49122(12) 0.88125(11) 0.0102(3) Uani d 1 . .
C C1 0.81752(13) 0.33305(13) 0.70628(11) 0.0109(3) Uani d 1 . .
C C2 0.76674(13) 0.47406(13) 0.74394(11) 0.0103(3) Uani d 1 . .
H H2 0.8249(18) 0.541(2) 0.7165(17) 0.012(4) Uiso d 1 . .
N N1 0.63426(11) 0.50005(11) 0.68844(10) 0.0103(2) Uani d 1 . .
H H1A 0.643(2) 0.4967(19) 0.605(2) 0.019(5) Uiso d 1 . .
H H1B 0.602(2) 0.584(2) 0.7085(18) 0.023(5) Uiso d 1 . .
H H1C 0.568(2) 0.438(2) 0.7126(19) 0.022(5) 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'
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
H4 N2 H3 . . 108(2) ?
H4 N2 H5 . . 113(2) ?
H3 N2 H5 . . 107(2) ?
H4 N2 H6 . . 107(2) ?
H3 N2 H6 . . 109.4(19) ?
H5 N2 H6 . . 111.5(19) ?
O3 C3 O4 . . 127.55(12) ?
O3 C3 C2 . . 116.89(11) ?
O4 C3 C2 . . 115.55(11) ?
O1 C1 O2 . . 124.87(12) ?
O1 C1 C2 . . 117.71(11) ?
O2 C1 C2 . . 117.40(11) ?
N1 C2 C1 . . 109.56(10) ?
N1 C2 C3 . . 109.98(10) ?
C1 C2 C3 . . 113.00(10) ?
N1 C2 H2 . . 107.1(11) ?
C1 C2 H2 . . 110.1(12) ?
C3 C2 H2 . . 106.8(12) ?
C2 N1 H1A . . 109.2(13) ?
C2 N1 H1B . . 111.4(13) ?
H1A N1 H1B . . 108.0(17) ?
C2 N1 H1C . . 113.2(12) ?
H1A N1 H1C . . 109.0(18) ?
H1B N1 H1C . . 105.9(18) ?
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
N2 H4 . 0.83(3) ?
N2 H3 . 0.85(2) ?
N2 H5 . 0.88(2) ?
N2 H6 . 0.89(2) ?
O3 C3 . 1.2462(17) ?
O4 C3 . 1.2597(16) ?
O2 C1 . 1.2657(16) ?
O1 C1 . 1.2483(16) ?
C3 C2 . 1.5485(18) ?
C1 C2 . 1.5394(18) ?
C2 N1 . 1.4821(16) ?
C2 H2 . 0.93(2) ?
N1 H1A . 0.93(2) ?
N1 H1B . 0.91(2) ?
N1 H1C . 0.94(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
O1 C1 C2 N1 . . . . -2.96(16) ?
O2 C1 C2 N1 . . . . 175.49(11) ?
O1 C1 C2 C3 . . . . 120.05(13) ?
O2 C1 C2 C3 . . . . -61.50(15) ?
O3 C3 C2 N1 . . . . 10.44(15) ?
O4 C3 C2 N1 . . . . -169.89(10) ?
O3 C3 C2 C1 . . . . -112.34(12) ?
O4 C3 C2 C1 . . . . 67.33(14) ?
