##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'Jana2006 Version : 09/03/2010'
_journal_date_recd_electronic     2014-06-11
_journal_date_accepted     2014-08-09
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2014
_journal_volume     70
_journal_issue     10
_journal_page_first     927
_journal_page_last     933
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229614018269
_journal_coeditor_code     FM3021
_publ_contact_author_name     'Jan Fábry'
_publ_contact_author_address
;
Institute of Physics
Czech Academy of Sciences
Na Slovance 2
182 21 Praha 8
Czech Republic
;
_publ_contact_author_email     fabry@fzu.cz
_publ_contact_author_fax     '(420)2 8689 0527'
_publ_contact_author_phone     '(420)2 6605 2695'
_publ_section_title
;
Comparison of the hydrogen-bond atterns 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)
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Matulková, Irena'
;
Faculty of Science
Charles University in Prague
Hlavova 2030/8
128 43 Praha 2
Czech Republic
;
    'Císařová, Ivana'
;
Faculty of Science
Charles University in Prague
Hlavova 2030/8
128 43 Praha 2
Czech Republic
;
    'Němec, Ivan'
;
Faculty of Science
Charles University in Prague
Hlavova 2030/8
128 43 Praha 2
Czech Republic
;
    'Fábry, Jan'
;
Institute of Physics
Czech Academy of Sciences
Na Slovance 2
182 21 Praha 8
Czech Republic
;
_publ_section_synopsis
;
2-Amino-1,3,4-thiadiazole--succinic acid (1/2) differs from the other title
compounds not only in the molar ratio of the base and acid (1:2) but also in
its hydrogen-bonding pattern. In the remaining compounds, with an equimolar
ratio of base and acid (1:1), the most prominent feature is an
R₂²(8) graph-set motif. This motif is formed by moderate-strength
N---H...O and O---H...N hydrogen bonds, except for 2-amino-1,3,4-thiadiazolium
hydrogen oxalate, where only N---H...O hydrogen bonds are present, in
agreement with the higher acidity of oxalic acid. There are S...O non-bonding
interactions in all of the structures. Despite these similarities, the packing
patterns are quite different in the four structures.
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1018659'
_chemical_name_systematic
;
2-amino-1,3,4-thiadiazolium hydrogen oxalate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C2 H4 N3 S1+, C2 H1 O4-'
_chemical_formula_sum     'C4 H5 N3 O4 S1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C2 H4 N3 S1 + , C2 H1 O4 -'
_chemical_formula_weight     191.2
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,y+1/2,-z+1/2
    3 -x,-y,-z
    4 x,-y+1/2,z+1/2
_cell_length_a     3.68480(10)
_cell_length_b     10.0617(2)
_cell_length_c     18.9595(4)
_cell_angle_alpha     90
_cell_angle_beta     94.9820(10)
_cell_angle_gamma     90
_cell_volume     700.27(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4550
_cell_measurement_theta_min     2.96
_cell_measurement_theta_max     30.03
_cell_measurement_temperature     150(2)
_cell_special_details
;
;
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.56
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.8126
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     0.44
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2013)'
_exptl_absorpt_correction_T_min     0.7898
_exptl_absorpt_correction_T_max     0.9110
_exptl_special_details     ?
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_device     ?
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6984
_diffrn_reflns_av_R_equivalents     0.0188
_diffrn_reflns_av_sigmaI/netI     0.0139
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     30.03
_diffrn_reflns_theta_full     30.03
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     26
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
The diffractions for which |Iₒ - Ic|/w > 15 have been discarded from the
refinement. The diffractions with θ < 3° which could have been affected by
shadowing by the beam-stop were excluded from the refinement as well.
The condition for exclusion of the diffractions
for which |Io~ - Ic~|/w > 15.
The following diffractions have been from the refinement:
   h   k   l     Iₒ      σ(Iₒ)  observed/unobserved
   1   2   0     25.56     0.51              o
   0   3   1     53.44     0.63              o
  -2   0   2     65.31     1.27              o
   0   0   2    -6.33      0.25              u
   0   2   2    -0.13      0.13              u
   0   5   5     33.66     0.63              o
   0   5   9     51.13     1.14              o
Indicators of the refinement with these diffractions
included into the refinement:
 _refine_ls_R_factor_gt                   0.0238
 _refine_ls_wR_factor_gt                  0.0724
 _refine_ls_R_factor_all                  0.0267
 _refine_ls_wR_factor_ref                 0.0763
 _refine_ls_goodness_of_fit_ref           2.41
 _refine_ls_goodness_of_fit_gt            2.40
;
_reflns_number_total     2031
_reflns_number_gt     1856
_reflns_threshold_expression     I>3σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0257
_refine_ls_R_factor_gt     0.0228
_refine_ls_wR_factor_gt     0.0660
_refine_ls_wR_factor_ref     0.0673
_refine_ls_goodness_of_fit_ref     2.13
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     2031
_refine_ls_number_parameters     125
_refine_ls_number_restraints     2
_refine_ls_number_constraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w = 1/(σ²(I)+0.0004I²)'
_refine_ls_shift/su_max     0.0258
_refine_ls_shift/su_mean     0.0016
_refine_diff_density_max     0.35
_refine_diff_density_min     -0.19
_refine_ls_extinction_method
                      'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       28E2(5)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement
                                 'JANA2006 (Petříček et al., 2014)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005), PLATON (Spek, 2009) and
JANA2006 (Petříček et al., 2014)
;
_computing_publication_material
                                 'JANA2006 (Petříček et al., 2014)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.79484(6) 0.02922(2) 0.329515(12) 0.01298(8) Uani d . 1 4 . .
    C C1 0.7051(3) 0.01362(10) 0.41761(5) 0.0155(3) Uani d . 1 4 . .
    H H1C1 0.745(3) -0.0672(13) 0.4420(7) 0.0186 Uiso d . 1 4 . .
    N N1 0.5730(2) 0.11718(8) 0.44587(4) 0.0165(2) Uani d . 1 4 . .
    N N2 0.5392(2) 0.21836(8) 0.39696(4) 0.0145(2) Uani d . 1 4 . .
    H H1N2 0.431(3) 0.2958(13) 0.4086(7) 0.0174 Uiso d . 1 4 . .
    C C2 0.6399(2) 0.19124(9) 0.33261(5) 0.0127(2) Uani d . 1 4 . .
    N N3 0.6252(3) 0.27729(9) 0.28034(5) 0.0197(3) Uani d . 1 4 . .
    H H1N3 0.677(3) 0.2547(13) 0.2384(5) 0.0237 Uiso d . 1 4 . .
    H H2N3 0.551(3) 0.3591(9) 0.2888(7) 0.0237 Uiso d . 1 4 . .
    O O1 0.3875(2) 0.52836(7) 0.32709(4) 0.0186(2) Uani d . 1 4 . .
    O O2 0.2010(2) 0.45203(7) 0.42940(4) 0.0179(2) Uani d . 1 4 . .
    C C3 0.2331(3) 0.53837(9) 0.38231(5) 0.0133(2) Uani d . 1 4 . .
    C C4 0.0620(3) 0.67582(9) 0.39569(5) 0.0139(2) Uani d . 1 4 . .
    O O3 0.0809(2) 0.76780(7) 0.35515(4) 0.0209(2) Uani d . 1 4 . .
    O O4 -0.1070(2) 0.68824(7) 0.45397(4) 0.0182(2) Uani d . 1 4 . .
    H H1O4 -0.098(3) 0.6206(14) 0.4768(7) 0.0273 Uiso d . 1 4 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . . 1.7377(10) no
    S1 C2 . . 1.7300(9) no
    C1 H1C1 . . 0.941(13) no
    C1 N1 . . 1.2865(13) no
    N1 N2 . . 1.3755(11) no
    N2 H1N2 . . 0.911(13) no
    N2 C2 . . 1.3339(12) no
    C2 N3 . . 1.3135(12) no
    N3 H1N3 . . 0.864(10) no
    N3 H2N3 . . 0.886(10) no
    H1N3 H2N3 . . 1.519(16) no
    O1 C3 . . 1.2382(12) no
    O2 C3 . . 1.2586(12) no
    C3 C4 . . 1.5500(13) no
    C4 O3 . . 1.2089(12) no
    C4 O4 . . 1.3207(12) no
    O4 H1O4 . . 0.805(14) no
    S1 O1 . 2_645 2.9868(8) no
    S1 O3 . 1_645 2.8595(7) no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    S1 C1 H1C1 . . . 121.1(8) no
    S1 C1 N1 . . . 115.95(7) no
    H1C1 C1 N1 . . . 122.9(8) no
    C1 N1 N2 . . . 109.51(8) no
    N1 N2 H1N2 . . . 119.0(8) no
    N1 N2 C2 . . . 116.69(8) no
    H1N2 N2 C2 . . . 124.0(8) no
    S1 C2 N2 . . . 110.03(7) no
    S1 C2 N3 . . . 125.99(8) no
    N2 C2 N3 . . . 123.97(9) no
    C2 N3 H1N3 . . . 121.6(9) no
    C2 N3 H2N3 . . . 118.0(8) no
    H1N3 N3 H2N3 . . . 120.4(12) no
    O1 C3 O2 . . . 128.47(9) no
    O1 C3 C4 . . . 115.73(8) no
    O2 C3 C4 . . . 115.79(8) no
    C3 C4 O3 . . . 122.16(9) no
    C3 C4 O4 . . . 116.71(8) no
    O3 C4 O4 . . . 121.13(9) no
    O3 C4 H1O4 . . . 146.0(5) no
    C4 O4 H1O4 . . . 111.6(10) no
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
    C3 C4 O4 H1O4 . . . . 0.9(10) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O4 H1O4 O2 . . . 0.809(14) 2.245(14) 2.6914(10) 115.2(12) no
    O4 H1O4 O2 . . 3_566 0.809(14) 1.990(14) 2.6709(10) 141.4(14) yes
    N2 H1N2 O2 . . . 0.923(13) 1.833(13) 2.7553(11) 177.7(11) yes
    N3 H1N3 O1 . . 2_645 0.867(10) 2.594(13) 3.2260(11) 130.6(11) no
    N3 H1N3 O3 . . 2_645 0.867(10) 2.055(11) 2.8745(12) 157.4(12) yes
    N3 H2N3 O1 . . . 0.888(10) 1.966(10) 2.8407(11) 168.4(12) yes
    C1 H1C1 O4 . . 1_645 0.946(13) 2.520(13) 3.4044(12) 155.6(11) yes
    C1 H1C1 N1 . . 3_656 0.946(13) 2.563(13) 3.1531(13) 120.7(10) yes
data_II
_database_code_depnum_ccdc_archive     'CCDC 1018660'
_chemical_name_systematic
;
2-Amino-1,3,4-thiadiazole--succinic acid (1/2)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C2 H3 N3 S1, 2(C4 H6 O4)'
_chemical_formula_sum     'C10 H15 N3 O8 S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C2 H3 N3 S1 , 2C4 H6 O4'
_chemical_formula_weight     337.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,y+1/2,-z+1/2
    3 -x,-y,-z
    4 x,-y+1/2,z+1/2
_cell_length_a     11.9022(3)
_cell_length_b     5.3284(2)
_cell_length_c     14.3267(4)
_cell_angle_alpha     90
_cell_angle_beta     96.3750(10)
_cell_angle_gamma     90
_cell_volume     902.98(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3671
_cell_measurement_theta_min     3.17
_cell_measurement_theta_max     27.44
_cell_measurement_temperature     150(2)
_cell_special_details
;
;
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.16
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     2.4811
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.432
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2013)'
_exptl_absorpt_correction_T_min     0.8670
_exptl_absorpt_correction_T_max     0.9451
_exptl_special_details     ?
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_device     ?
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7307
_diffrn_reflns_av_R_equivalents     0.0169
_diffrn_reflns_av_sigmaI/netI     0.016
_diffrn_reflns_theta_min     2.86
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
The diffractions for which |Iₒ - Ic|/w > 15 have been discarded from the
refinement. The diffractions with θ < 3° which could have been affected by
shadowing by the beam-stop were excluded from the refinement as well.
The condition for exclusion of the diffractions
for which |Io~ - Ic~|/w > 15.
The following diffraction has been removed
from the refinement:
   h   k   l     Iₒ      σ(Iₒ)  observed/unobserved
  -3   2   3       73.50     1.24            o
Indicators of the refinement with this diffraction
included into the refinement:
_refine_ls_R_factor_gt                   0.0303
_refine_ls_wR_factor_gt                  0.0795
_refine_ls_R_factor_all                  0.0353
_refine_ls_wR_factor_ref                 0.0822
_refine_ls_goodness_of_fit_ref           2.26
_refine_ls_goodness_of_fit_gt            2.35
;
_reflns_number_total     2059
_reflns_number_gt     1802
_reflns_threshold_expression     I>3σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0349
_refine_ls_R_factor_gt     0.0300
_refine_ls_wR_factor_gt     0.0781
_refine_ls_wR_factor_ref     0.0810
_refine_ls_goodness_of_fit_ref     2.23
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     2059
_refine_ls_number_parameters     142
_refine_ls_number_restraints     2
_refine_ls_number_constraints     21
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w = 1/(σ²(I)+0.0004I²)'
_refine_ls_shift/su_max     0.0151
_refine_ls_shift/su_mean     0.0012
_refine_diff_density_max     0.33
_refine_diff_density_min     -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement
                                 'JANA2006 (Petříček et al., 2006)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005), PLATON (Spek, 2009) and
JANA2006 (Petříček et al., 2014)
;
_computing_publication_material
                                 'JANA2006 (Petříček et al., 2014)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.21112(3) 0.42956(7) 0.31351(3) 0.02313(13) Uani d . 1 . .
    C C1 0.16065(12) 0.6838(3) 0.24681(11) 0.0235(5) Uani d . 1 . .
    H H1C1 0.0986(12) 0.783(3) 0.2648(11) 0.0282 Uiso d . 1 . .
    N N1 0.21467(9) 0.7284(2) 0.17521(8) 0.0207(4) Uani d . 1 . .
    N N2 0.30255(9) 0.5626(2) 0.16689(8) 0.0179(4) Uani d . 1 . .
    C C2 0.31147(11) 0.3944(3) 0.23516(9) 0.0172(4) Uani d . 1 . .
    N N3 0.39064(11) 0.2166(2) 0.24449(9) 0.0250(4) Uani d . 1 . .
    H H1N3 0.3916(13) 0.095(2) 0.2880(9) 0.03 Uiso d . 1 . .
    H H2N3 0.4434(11) 0.218(3) 0.2049(9) 0.03 Uiso d . 1 . .
    C C3 0.45445(10) 0.5775(2) 0.51965(9) 0.0154(4) Uani d . 1 . .
    H H1C3 0.389845 0.467865 0.530056 0.0185 Uiso d . 1 . .
    H H2C3 0.483816 0.643239 0.582263 0.0185 Uiso d . 1 . .
    C C4 0.41353(10) 0.7917(3) 0.45670(9) 0.0141(4) Uani d . 1 . .
    O O1 0.43435(7) 0.80915(19) 0.37551(6) 0.0188(3) Uani d . 1 . .
    O O2 0.35066(8) 0.96516(19) 0.49118(7) 0.0187(3) Uani d . 1 . .
    H H1O2 0.3419(13) 0.947(3) 0.5536(12) 0.028 Uiso d . 1 . .
    C C5 0.04858(10) 0.4182(3) -0.01168(10) 0.0188(4) Uani d . 1 . .
    H H1C5 0.115705 0.524276 -0.017612 0.0226 Uiso d . 1 . .
    H H2C5 0.028961 0.339486 -0.073956 0.0226 Uiso d . 1 . .
    C C6 0.07850(11) 0.2177(3) 0.06046(10) 0.0173(4) Uani d . 1 . .
    O O3 0.16923(9) 0.0877(2) 0.04430(8) 0.0272(4) Uani d . 1 . .
    H H1O3 0.1828(14) -0.030(3) 0.0871(13) 0.0408 Uiso d . 1 . .
    O O4 0.02640(9) 0.1755(2) 0.12657(8) 0.0314(4) Uani d . 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . . 1.7266(16) no
    S1 C2 . . 1.7376(14) no
    C1 H1C1 . . 0.966(16) no
    C1 N1 . . 1.292(2) no
    N1 N2 . . 1.3843(16) no
    N2 C2 . . 1.3220(18) no
    C2 N3 . . 1.3326(19) no
    N3 H1N3 . . 0.900(13) no
    N3 H2N3 . . 0.892(14) no
    H1N3 H2N3 . . 1.55(2) no
    C3 C3 . 3_666 1.5198(18) no
    C3 H1C3 . . 0.99 no
    C3 H2C3 . . 0.99 no
    C3 C4 . . 1.5021(18) no
    H1C3 H2C3 . . 1.5805 no
    C4 O1 . . 1.2194(16) no
    C4 O2 . . 1.3192(17) no
    O2 H1O2 . . 0.917(17) no
    C5 C5 . 3_565 1.5152(19) no
    C5 H1C5 . . 0.99 no
    C5 H2C5 . . 0.99 no
    C5 C6 . . 1.5013(19) no
    H1C5 H2C5 . . 1.5818 no
    C6 O3 . . 1.3248(17) no
    C6 O4 . . 1.2094(18) no
    O3 H1O3 . . 0.880(18) no
    S1 O3 . 4_555 3.3995(12) no
    S1 O4 . 2_555 3.3145(12) no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    S1 C1 H1C1 . . . 120.7(10) no
    S1 C1 N1 . . . 114.25(11) no
    H1C1 C1 N1 . . . 125.0(10) no
    C1 N1 N2 . . . 113.47(12) no
    N1 N2 C2 . . . 111.61(12) no
    N1 N2 H1O2 . . 4_564 112.5(5) no
    C2 N2 H1O2 . . 4_564 131.5(5) no
    S1 C2 N2 . . . 113.60(10) no
    S1 C2 N3 . . . 122.74(11) no
    N2 C2 N3 . . . 123.65(13) no
    C2 N3 H1N3 . . . 122.5(10) no
    C2 N3 H2N3 . . . 118.0(10) no
    H1N3 N3 H2N3 . . . 119.6(14) no
    C3 C3 H1C3 3_666 . . 109.47 no
    C3 C3 H2C3 3_666 . . 109.47 no
    C3 C3 C4 3_666 . . 112.80(11) no
    H1C3 C3 H2C3 . . . 105.92 no
    H1C3 C3 C4 . . . 109.47 no
    H2C3 C3 C4 . . . 109.47 no
    C3 C4 O1 . . . 122.95(12) no
    C3 C4 O2 . . . 117.85(12) no
    O1 C4 O2 . . . 119.19(12) no
    C4 O2 H1O2 . . . 114.9(10) no
    N2 H1o2 O2 4_565 . . 170.0(15) no
    C5 C5 H1C5 3_565 . . 109.47 no
    C5 C5 H2C5 3_565 . . 109.47 no
    C5 C5 C6 3_565 . . 112.69(12) no
    H1C5 C5 H2C5 . . . 106.04 no
    H1C5 C5 C6 . . . 109.47 no
    H2C5 C5 C6 . . . 109.47 no
    C5 C6 O3 . . . 112.79(12) no
    C5 C6 O4 . . . 124.64(12) no
    O3 C6 O4 . . . 122.57(13) no
    C6 O3 H1O3 . . . 109.9(12) no
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
    C5 C6 O3 H1O3 . . . . -178.5(12) no
    C3 C4 O2 H1o2 . . . . 4.9(11) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O2 H1O2 N2 . . 4_565 0.909(17) 1.747(17) 2.6470(16) 170.1(15) yes
    O3 H1O3 N1 . . 1_545 0.873(18) 1.820(18) 2.6926(16) 178.4(17) yes
    N3 H1N3 O1 . . 1_545 0.900(13) 2.001(13) 2.8794(16) 164.9(14) yes
    N3 H2N3 O1 . . 2_645 0.893(14) 2.012(14) 2.8869(17) 166.1(15) yes
    C1 H1C1 O4 . . 2_555 0.965(16) 2.340(16) 3.0243(19) 127.3(12) yes
data_III
_database_code_depnum_ccdc_archive     'CCDC 1018661'
_chemical_name_systematic
;
2-Amino-1,3,4-thiadiazole--glutaric acid (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C2 H3 N3 S1, C5 H8 O4'
_chemical_formula_sum     'C7 H11 N3 O4 S1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C2 H3 N3 S1 , C5 H8 O4'
_chemical_formula_weight     233.2
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
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
_cell_length_a     7.1620(2)
_cell_length_b     10.0096(2)
_cell_length_c     27.8847(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1999.02(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3659
_cell_measurement_theta_min     2.92
_cell_measurement_theta_max     27.41
_cell_measurement_temperature     150(2)
_cell_special_details
;
;
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.14
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.5495
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.323
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2013)'
_exptl_absorpt_correction_T_min     0.8759
_exptl_absorpt_correction_T_max     0.9570
_exptl_special_details     ?
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_device     ?
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9941
_diffrn_reflns_av_R_equivalents     0.025
_diffrn_reflns_av_sigmaI/netI     0.02
_diffrn_reflns_theta_min     1.46
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     1.0
_diffrn_measured_fraction_theta_full     1.0
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     36
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
The diffractions for which |Iₒ - Ic|/w > 15 have been discarded from the
refinement. The diffractions with θ < 3° which could have been affected by
shadowing by the beam-stop were excluded from the refinement as well.
The condition for exclusion of the diffractions
for which |Io~ - Ic~|/w > 15.
The following diffraction has been from the refinement:
   h   k   l     Iₒ      σ(Iₒ)  observed/unobserved
   0   0   2     289.46      5.13           o
Indicators of the refinement with this diffraction
included into the refinement:
_refine_ls_R_factor_gt                   0.0277
_refine_ls_wR_factor_gt                  0.0673
_refine_ls_R_factor_all                  0.0363
_refine_ls_wR_factor_ref                 0.0701
_refine_ls_goodness_of_fit_ref           1.73
_refine_ls_goodness_of_fit_gt            1.85
;
_reflns_number_total     2295
_reflns_number_gt     1881
_reflns_threshold_expression     'I>3σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0361
_refine_ls_R_factor_gt     0.0275
_refine_ls_wR_factor_gt     0.0646
_refine_ls_wR_factor_ref     0.0674
_refine_ls_goodness_of_fit_ref     1.66
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     2295
_refine_ls_number_parameters     152
_refine_ls_number_restraints     4
_refine_ls_number_constraints     29
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w=1/(σ²(I)+0.0004I²)'
_refine_ls_shift/su_max     0.0415
_refine_ls_shift/su_mean     0.0032
_refine_diff_density_max     0.23
_refine_diff_density_min     -0.22
_refine_ls_extinction_method
                      'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       24E2(5)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement
                                 'JANA2006 (Petříček et al., 2014)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005), PLATON (Spek, 2009) and
JANA2006 (Petříček et al., 2014)
;
_computing_publication_material
                                 'JANA2006 (Petříček et al., 2014)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    _atom_site_aniso_type_symbol
    S1 0.03127(19) 0.01649(17) 0.01386(18) 0.00020(13) 0.00432(14) -0.00241(14)
                                                                               S
    C1 0.0335(8) 0.0182(7) 0.0140(7) -0.0009(5) 0.0013(6) 0.0011(6) C
    N1 0.0299(6) 0.0182(5) 0.0127(6) -0.0001(5) 0.0003(5) 0.0008(5) N
    N2 0.0265(6) 0.0151(5) 0.0120(6) -0.0003(4) 0.0009(5) 0.0010(5) N
    C2 0.0185(6) 0.0185(6) 0.0131(7) -0.0005(5) 0.0006(5) -0.0022(5) C
    N3 0.0364(7) 0.0154(5) 0.0166(6) 0.0007(5) 0.0070(5) 0.0001(5) N
    O1 0.0424(6) 0.0166(5) 0.0141(5) 0.0059(4) 0.0082(4) 0.0021(4) O
    O2 0.0380(6) 0.0145(5) 0.0182(5) 0.0018(4) 0.0050(5) -0.0004(4) O
    C3 0.0181(6) 0.0179(6) 0.0131(7) -0.0001(5) -0.0018(5) 0.0012(5) C
    C4 0.0285(7) 0.0155(6) 0.0151(7) 0.0028(5) 0.0027(6) 0.0001(6) C
    C5 0.0212(6) 0.0162(6) 0.0125(7) 0.0010(5) -0.0001(5) -0.0003(5) C
    C6 0.0235(6) 0.0162(6) 0.0134(7) 0.0021(5) 0.0010(5) 0.0014(5) C
    C7 0.0190(6) 0.0172(6) 0.0135(7) -0.0024(5) -0.0034(6) -0.0014(5) C
    O3 0.0319(5) 0.0149(4) 0.0135(5) -0.0002(4) 0.0028(4) 0.0004(4) O
    O4 0.0368(6) 0.0140(5) 0.0188(5) -0.0009(4) -0.0008(5) 0.0012(4) O
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _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_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_2
    _geom_angle_site_symmetry_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_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
    C4 C3 O1 H1O1 . . . . 177.3(11) no
    C6 C7 O3 H1O3 . . . . 6.8(11) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
data_IV
_database_code_depnum_ccdc_archive     'CCDC 1018662'
_chemical_name_systematic
;
2-amino-1,3,4-thiadiazole--adipic acid (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C2 H3 N3 S, C6 H10 O4'
_chemical_formula_sum     'C8 H13 N3 O4 S1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C2 H3 N3 S , C6 H10 O4'
_chemical_formula_weight     247.3
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,y+1/2,-z+1/2
    3 -x,-y,-z
    4 x,-y+1/2,z+1/2
_cell_length_a     11.1790(2)
_cell_length_b     10.2187(2)
_cell_length_c     9.6532(2)
_cell_angle_alpha     90
_cell_angle_beta     98.1160(10)
_cell_angle_gamma     90
_cell_volume     1091.69(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4518
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     30.02
_cell_measurement_temperature     150(2)
_cell_special_details
;
;
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.23
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.301
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2013)'
_exptl_absorpt_correction_T_min     0.8997
_exptl_absorpt_correction_T_max     0.9329
_exptl_special_details     ?
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_device     ?
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10441
_diffrn_reflns_av_R_equivalents     0.0204
_diffrn_reflns_av_sigmaI/netI     0.0209
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     30.02
_diffrn_reflns_theta_full     30.02
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     10
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
The diffractions for which |Iₒ - Ic|/w > 15 have been discarded from the
refinement. The diffractions with θ < 3° which could have been affected by
shadowing by the beam-stop were excluded from the refinement as well.
The condition for exclusion of the diffractions
for which |Io~ - Ic~|/w > 15.
The following diffraction has been removed from the refinement:
   h   k   l     Iₒ      σ(Iₒ)  observed/unobserved
  -3   3   2     297.44     3.31          o
Indicators of the refinement with this diffraction
included into the refinement:
_refine_ls_R_factor_gt                   0.0292
_refine_ls_wR_factor_gt                  0.0738
_refine_ls_R_factor_all                  0.0380
_refine_ls_wR_factor_ref                 0.0763
_refine_ls_goodness_of_fit_ref           1.90
_refine_ls_goodness_of_fit_gt            2.04
;
_reflns_number_total     3182
_reflns_number_gt     2616
_reflns_threshold_expression     'I>3σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0380
_refine_ls_R_factor_gt     0.0292
_refine_ls_wR_factor_gt     0.0729
_refine_ls_wR_factor_ref     0.0754
_refine_ls_goodness_of_fit_ref     1.88
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     3182
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_number_constraints     37
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w=1/(σ²(I)+0.0004I²)'
_refine_ls_shift/su_max     0.0217
_refine_ls_shift/su_mean     0.0021
_refine_diff_density_max     0.30
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     'none'
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement
                                 'JANA2006 (Petříček et al., 2014)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005), PLATON (Spek, 2009) and
JANA2006 (Petříček et al., 2014)
;
_computing_publication_material
                                 'JANA2006 (Petříček et al., 2014)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.92798(2) 0.58212(3) -0.16637(3) 0.01828(8) Uani d . 1 4 . .
    C C1 0.93970(10) 0.74918(11) -0.18192(12) 0.0189(3) Uani d . 1 4 . .
    H H1c1 0.9901(11) 0.7888(13) -0.2422(14) 0.0227 Uiso d . 1 4 . .
    N N1 0.87422(8) 0.81559(9) -0.10641(10) 0.0189(3) Uani d . 1 4 . .
    N N2 0.80693(8) 0.73784(9) -0.02887(10) 0.0176(3) Uani d . 1 4 . .
    C C2 0.82499(9) 0.61224(11) -0.05088(12) 0.0167(3) Uani d . 1 4 . .
    N N3 0.77004(9) 0.51588(10) 0.00746(12) 0.0267(3) Uani d . 1 4 . .
    H H1n3 0.7232(10) 0.5383(13) 0.0692(11) 0.032 Uiso d . 1 4 . .
    H H2n3 0.7877(12) 0.4339(9) -0.0117(14) 0.032 Uiso d . 1 4 . .
    O O1 0.64820(7) 0.82007(8) 0.14962(9) 0.0221(3) Uani d . 1 4 . .
    H H1o1 0.6971(13) 0.7895(13) 0.0965(15) 0.0331 Uiso d . 1 4 . .
    O O2 0.61559(8) 0.60863(8) 0.19340(10) 0.0314(3) Uani d . 1 4 . .
    C C3 0.59450(9) 0.72358(11) 0.20916(12) 0.0186(3) Uani d . 1 4 . .
    C C4 0.50333(9) 0.77157(11) 0.29840(11) 0.0179(3) Uani d . 1 4 . .
    H H1c4 0.449227 0.836298 0.245109 0.0215 Uiso d . 1 4 . .
    H H2c4 0.545406 0.819773 0.380026 0.0215 Uiso d . 1 4 . .
    C C5 0.42806(9) 0.66197(11) 0.34890(12) 0.0191(3) Uani d . 1 4 . .
    H H1c5 0.481604 0.600867 0.40831 0.0229 Uiso d . 1 4 . .
    H H2c5 0.388588 0.611549 0.267467 0.0229 Uiso d . 1 4 . .
    C C6 0.33238(9) 0.71488(11) 0.43140(12) 0.0170(3) Uani d . 1 4 . .
    H H1c6 0.371252 0.770903 0.508575 0.0204 Uiso d . 1 4 . .
    H H2c6 0.276896 0.773258 0.370827 0.0204 Uiso d . 1 4 . .
    C C7 0.25987(9) 0.60774(11) 0.49075(11) 0.0185(3) Uani d . 1 4 . .
    H H1c7 0.217882 0.554275 0.413197 0.0223 Uiso d . 1 4 . .
    H H2c7 0.315703 0.546357 0.546769 0.0223 Uiso d . 1 4 . .
    C C8 0.16922(9) 0.65874(10) 0.57891(12) 0.0170(3) Uani d . 1 4 . .
    O O3 0.10549(8) 0.57162(8) 0.63762(10) 0.0265(3) Uani d . 1 4 . .
    H H1o3 0.1194(12) 0.4948(14) 0.6180(14) 0.0397 Uiso d . 1 4 . .
    O O4 0.15287(7) 0.77487(8) 0.59926(9) 0.0228(3) Uani d . 1 4 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    _atom_site_aniso_type_symbol
    S1 0.02002(13) 0.01443(15) 0.02273(15) 0.00142(10) 0.01118(10) -0.00105(11)
                                                                               S
    C1 0.0200(5) 0.0158(6) 0.0222(6) -0.0013(4) 0.0078(4) 0.0008(5) C
    N1 0.0211(4) 0.0146(5) 0.0224(5) -0.0013(4) 0.0082(4) 0.0001(4) N
    N2 0.0211(4) 0.0127(5) 0.0211(5) -0.0005(3) 0.0098(4) -0.0003(4) N
    C2 0.0175(5) 0.0158(5) 0.0181(5) 0.0019(4) 0.0073(4) -0.0001(4) C
    N3 0.0347(5) 0.0128(5) 0.0385(6) 0.0016(4) 0.0257(5) 0.0004(5) N
    O1 0.0251(4) 0.0187(4) 0.0257(5) -0.0002(3) 0.0147(3) 0.0011(4) O
    O2 0.0383(5) 0.0161(4) 0.0464(6) -0.0008(4) 0.0291(4) -0.0026(4) O
    C3 0.0176(5) 0.0196(6) 0.0196(5) -0.0009(4) 0.0066(4) -0.0007(5) C
    C4 0.0185(5) 0.0171(6) 0.0198(5) 0.0003(4) 0.0086(4) -0.0016(5) C
    C5 0.0197(5) 0.0166(6) 0.0234(6) 0.0009(4) 0.0115(4) -0.0011(5) C
    C6 0.0183(5) 0.0152(5) 0.0192(5) 0.0003(4) 0.0083(4) -0.0001(4) C
    C7 0.0205(5) 0.0160(6) 0.0211(6) 0.0001(4) 0.0096(4) -0.0022(5) C
    C8 0.0183(5) 0.0153(5) 0.0184(5) -0.0003(4) 0.0067(4) 0.0000(5) C
    O3 0.0350(4) 0.0117(4) 0.0384(5) 0.0003(3) 0.0250(4) 0.0012(4) O
    O4 0.0283(4) 0.0125(4) 0.0308(5) 0.0003(3) 0.0156(3) -0.0005(4) O
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . . 1.7203(12) no
    S1 C2 . . 1.7394(12) no
    C1 H1c1 . . 0.955(14) no
    C1 N1 . . 1.2956(15) no
    N1 N2 . . 1.3843(14) no
    N2 C2 . . 1.3211(14) no
    C2 N3 . . 1.3273(16) no
    N3 H1n3 . . 0.878(12) no
    N3 H2n3 . . 0.886(10) no
    H1n3 H2n3 . . 1.558(17) no
    O1 H1o1 . . 0.859(15) no
    O1 C3 . . 1.3268(14) no
    O2 C3 . . 1.2119(14) no
    C3 C4 . . 1.5064(16) no
    C4 H1c4 . . 0.99 no
    C4 H2c4 . . 0.99 no
    C4 C5 . . 1.5217(16) no
    H1c4 H2c4 . . 1.5765 no
    C5 H1c5 . . 0.99 no
    C5 H2c5 . . 0.99 no
    C5 C6 . . 1.5203(16) no
    H1c5 H2c5 . . 1.5945 no
    C6 H1c6 . . 0.99 no
    C6 H2c6 . . 0.99 no
    C6 C7 . . 1.5215(16) no
    H1c6 H2c6 . . 1.5765 no
    C7 H1c7 . . 0.99 no
    C7 H2c7 . . 0.99 no
    C7 C8 . . 1.5055(16) no
    H1c7 H2c7 . . 1.5706 no
    C8 O3 . . 1.3173(14) no
    C8 O4 . . 1.2208(13) no
    O3 H1o3 . . 0.827(14) no
    S1 O3 . 1_654 2.9308(10) yes
    S1 O4 . 2_645 3.3556(8) yes
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    S1 C1 H1c1 . . . 122.2(8) no
    S1 C1 N1 . . . 114.49(9) no
    H1c1 C1 N1 . . . 123.3(8) no
    C1 N1 N2 . . . 113.39(9) no
    N1 N2 C2 . . . 111.32(9) no
    S1 C2 N2 . . . 113.89(8) no
    S1 C2 N3 . . . 121.91(9) no
    N2 C2 N3 . . . 124.20(11) no
    C2 N3 H1n3 . . . 116.8(9) no
    C2 N3 H2n3 . . . 118.9(9) no
    H1n3 N3 H2n3 . . . 124.1(12) no
    H1o1 O1 C3 . . . 110.7(9) no
    O1 C3 O2 . . . 123.91(11) no
    O1 C3 C4 . . . 112.95(10) no
    O2 C3 C4 . . . 123.14(11) no
    C3 C4 H1c4 . . . 109.47 no
    C3 C4 H2c4 . . . 109.47 no
    C3 C4 C5 . . . 113.14(9) no
    H1c4 C4 H2c4 . . . 105.54 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 . . . 111.58(9) no
    H1c5 C5 H2c5 . . . 107.28 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 . . . 113.14(9) no
    H1c6 C6 H2c6 . . . 105.54 no
    H1c6 C6 C7 . . . 109.47 no
    H2c6 C6 C7 . . . 109.47 no
    C6 C7 H1c7 . . . 109.47 no
    C6 C7 H2c7 . . . 109.47 no
    C6 C7 C8 . . . 113.62(9) no
    H1c7 C7 H2c7 . . . 104.98 no
    H1c7 C7 C8 . . . 109.47 no
    H2c7 C7 C8 . . . 109.47 no
    C7 C8 O3 . . . 117.22(9) no
    C7 C8 O4 . . . 123.75(10) no
    O3 C8 O4 . . . 119.04(10) no
    C8 O3 H1o3 . . . 114.3(10) no
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
    C4 C3 O1 H1o1 . . . . -177.3(9) no
    C7 C8 O3 H1o3 . . . . -2.2(10) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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 O2 . . . 0.878(12) 1.951(12) 2.8242(15) 172.8(12) yes
    N3 H2N3 O4 . . 2_645 0.886(10) 1.989(11) 2.8496(13) 163.4(12) yes
    O1 H1O1 N2 . . . 0.859(15) 1.916(15) 2.7725(13) 174.6(13) yes
    O3 H1O3 N1 . . 2_645 0.827(14) 1.837(14) 2.6470(12) 165.9(14) yes
