#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/96/2019657.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_2019657
loop_
_publ_author_name
'Matulková, Irena'
'Císařová, Ivana'
'Němec, Ivan'
'Fábry, Jan'
_publ_section_title
;
 Comparison of the hydrogen-bond patterns in 2-amino-1,3,4-thiadiazolium
 hydrogen oxalate, 2-amino-1,3,4-thiadiazole--succinic acid (1/2),
 2-amino-1,3,4-thiadiazole--glutaric acid (1/1) and
 2-amino-1,3,4-thiadiazole--adipic acid (1/1)
;
_journal_coeditor_code           FM3021
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              927
_journal_page_last               933
_journal_paper_doi               10.1107/S2053229614018269
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C2 H3 N3 S1 , C5 H8 O4'
_chemical_formula_moiety         'C2 H3 N3 S1, C5 H8 O4'
_chemical_formula_sum            'C7 H11 N3 O4 S'
_chemical_formula_weight         233.2
_chemical_name_systematic
;
2-Amino-1,3,4-thiadiazole--glutaric acid (1/1)
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1620(2)
_cell_length_b                   10.0096(2)
_cell_length_c                   27.8847(7)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.92
_cell_volume                     1999.02(9)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005), PLATON (Spek, 2009) and
JANA2006 (Petříček et al., 2014)
;
_computing_publication_material  'JANA2006 (Petříček et al., 2014)'
_computing_structure_refinement  'JANA2006 (Petříček et al., 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.02
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9941
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_correction_T_min  0.8759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5495
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       24E2(5)
_refine_ls_extinction_method
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_ref   1.66
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    29
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.0415
_refine_ls_shift/su_mean         0.0032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                1881
_reflns_number_total             2295
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            fm3021sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 2019655--2019658.cif.'
_cod_original_formula_sum        'C7 H11 N3 O4 S1'
_cod_database_code               2019657
_cod_database_fobs_code          2019657
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z+1/2
8 -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_symmetry_multiplicity
S S1 -0.01814(5) 0.62369(3) 0.706072(12) 0.02054(10) Uani d 1 8
C C1 0.0041(2) 0.45455(13) 0.71681(5) 0.0219(4) Uani d 1 8
H H1c1 -0.021(2) 0.4166(16) 0.7463(6) 0.0263 Uiso d 1 8
N N1 0.05342(16) 0.38491(11) 0.68001(4) 0.0203(3) Uani d 1 8
N N2 0.07899(16) 0.46137(10) 0.63913(4) 0.0179(3) Uani d 1 8
C C2 0.04678(17) 0.58919(12) 0.64731(5) 0.0167(4) Uani d 1 8
N N3 0.06418(18) 0.68320(11) 0.61380(4) 0.0228(4) Uani d 1 8
H H1n3 0.1059(19) 0.6610(14) 0.5853(4) 0.0273 Uiso d 1 8
H H2n3 0.0391(19) 0.7658(9) 0.6201(6) 0.0273 Uiso d 1 8
O O1 0.19448(14) 0.35803(9) 0.55517(4) 0.0243(3) Uani d 1 8
H H1o1 0.156(2) 0.3957(14) 0.5805(4) 0.0365 Uiso d 1 8
O O2 0.19376(13) 0.56229(9) 0.52272(4) 0.0236(3) Uani d 1 8
C C3 0.22331(17) 0.44300(13) 0.51953(5) 0.0164(4) Uani d 1 8
C C4 0.29937(18) 0.37397(12) 0.47607(5) 0.0197(4) Uani d 1 8
H H1c4 0.416013 0.326533 0.48462 0.0236 Uiso d 1 8
H H2c4 0.214957 0.299991 0.466839 0.0236 Uiso d 1 8
C C5 0.33436(17) 0.46313(12) 0.43282(5) 0.0166(4) Uani d 1 8
H H1c5 0.214494 0.501256 0.42163 0.02 Uiso d 1 8
H H2c5 0.420073 0.53644 0.441948 0.02 Uiso d 1 8
C C6 0.42163(18) 0.38131(12) 0.39283(5) 0.0177(4) Uani d 1 8
H H1c6 0.535889 0.336889 0.404873 0.0212 Uiso d 1 8
H H2c6 0.339744 0.304541 0.385165 0.0212 Uiso d 1 8
C C7 0.46625(17) 0.45629(12) 0.34767(5) 0.0166(4) Uani d 1 8
O O3 0.54004(13) 0.38516(9) 0.31209(4) 0.0201(3) Uani d 1 8
H H1o3 0.543(2) 0.3021(9) 0.3172(6) 0.0302 Uiso d 1 8
O O4 0.44135(14) 0.57526(9) 0.34197(4) 0.0232(3) Uani d 1 8
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.000 0.000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.006 0.003 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.011 0.006 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
S 0.125 0.123 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
S1 C1 H1c1 122.6(10) no
S1 C1 N1 114.66(11) no
H1c1 C1 N1 122.7(10) no
C1 N1 N2 113.09(11) no
N1 N2 C2 111.73(11) no
S1 C2 N2 113.72(10) no
S1 C2 N3 123.10(10) no
N2 C2 N3 123.18(12) no
C2 N3 H1n3 119.2(9) no
C2 N3 H2n3 120.9(10) no
H1n3 N3 H2n3 119.9(14) no
H1o1 O1 C3 112.9(9) no
O1 C3 O2 123.28(12) no
O1 C3 C4 111.58(11) no
O2 C3 C4 125.14(12) no
C3 C4 H1c4 109.47 no
C3 C4 H2c4 109.47 no
C3 C4 C5 115.52(10) no
H1c4 C4 H2c4 102.66 no
H1c4 C4 C5 109.47 no
H2c4 C4 C5 109.47 no
C4 C5 H1c5 109.47 no
C4 C5 H2c5 109.47 no
C4 C5 C6 109.49(10) no
H1c5 C5 H2c5 109.45 no
H1c5 C5 C6 109.47 no
H2c5 C5 C6 109.47 no
C5 C6 H1c6 109.47 no
C5 C6 H2c6 109.47 no
C5 C6 C7 115.74(10) no
H1c6 C6 H2c6 102.37 no
H1c6 C6 C7 109.47 no
H2c6 C6 C7 109.47 no
C6 C7 O3 116.28(10) no
C6 C7 O4 124.69(12) no
O3 C7 O4 119.03(12) no
C7 O3 H1o3 114.4(10) no
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
S1 C1 . 1.7266(14) no
S1 C2 . 1.7379(14) no
C1 H1c1 . 0.923(17) no
C1 N1 . 1.2898(18) no
N1 N2 . 1.3853(16) no
N2 C2 . 1.3199(16) no
C2 N3 . 1.3318(17) no
N3 H1n3 . 0.879(11) no
N3 H2n3 . 0.865(10) no
H1n3 H2n3 . 1.509(18) no
O1 H1o1 . 0.845(12) no
O1 C3 . 1.3243(16) no
O2 C3 . 1.2160(15) no
C3 C4 . 1.4976(18) no
C4 H1c4 . 0.99 no
C4 H2c4 . 0.99 no
C4 C5 . 1.5210(18) no
C5 H1c5 . 0.99 no
C5 H2c5 . 0.99 no
C5 C6 . 1.5183(18) no
C6 H1c6 . 0.99 no
C6 H2c6 . 0.99 no
C6 C7 . 1.5002(18) no
C7 O3 . 1.3306(16) no
C7 O4 . 1.2146(15) no
O3 H1o3 . 0.844(9) no
S1 O3 2_565 2.9619(10) no
S1 O4 4_466 3.3105(9) no
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
N3 H1N3 O1 8_555 0.879(11) 2.577(14) 2.9535(15) 106.8(10) yes
N3 H2N3 O1 8_555 0.865(10) 2.788(14) 2.9535(15) 92.4(11) yes
N3 H1N3 O2 . 0.879(11) 2.101(12) 2.9627(16) 166.6(13) yes
N3 H2N3 O4 4_466 0.865(10) 2.034(12) 2.8531(15) 157.8(14) yes
O1 H1O1 N2 . 0.845(12) 1.848(12) 2.6898(15) 173.9(13) yes
O3 H1O3 N1 4_556 0.844(9) 1.875(9) 2.7139(14) 172.7(15) yes
O3 H1O3 N2 4_556 0.844(9) 2.916(11) 3.7362(14) 164.5(13) yes
C6 H1C6 O1 4_556 0.99 2.52 3.4148(16) 150.59 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
_geom_torsion_publ_flag
C4 C3 O1 H1O1 177.3(11) no
C6 C7 O3 H1O3 6.8(11) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061893
