#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/96/2019655.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_2019655
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 H4 N3 S1 + , C2 H1 O4 -'
_chemical_formula_moiety         'C2 H4 N3 S1+, C2 H1 O4-'
_chemical_formula_sum            'C4 H5 N3 O4 S'
_chemical_formula_weight         191.2
_chemical_name_systematic
;
2-amino-1,3,4-thiadiazolium hydrogen oxalate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 94.9820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.68480(10)
_cell_length_b                   10.0617(2)
_cell_length_c                   18.9595(4)
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.96
_cell_volume                     700.27(3)
_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 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6984
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.44
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.7898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.8126
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       28E2(5)
_refine_ls_extinction_method
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_ref   2.13
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    5
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.0258
_refine_ls_shift/su_mean         0.0016
_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          0.0660
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                1856
_reflns_number_total             2031
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            fm3021sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2019655--2019658.cif.'
_cod_original_formula_sum        'C4 H5 N3 O4 S1'
_cod_database_code               2019655
_cod_database_fobs_code          2019655
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
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 0.79484(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_
_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 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_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 . 1.7377(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_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
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
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
C3 C4 O4 H1O4 0.9(10) no
