#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239840.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_2239840
loop_
_publ_author_name
'Kim, Namhun'
'Kang, Sung Kwon'
_publ_section_title
;
 Crystal structure of a monoclinic polymorph of
 5-amino-1,3,4-thiadiazol-2(3H)-one
;
_journal_coeditor_code           TK5326
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o922
_journal_paper_doi               10.1107/S1600536814016055
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C2 H3 N3 O S'
_chemical_formula_moiety         'C2 H3 N3 O S'
_chemical_formula_sum            'C2 H3 N3 O S'
_chemical_formula_weight         117.13
_chemical_name_systematic
;
5-Amino-1,3,4-thiadiazol-2(3H)-one
;
_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'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.015(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   3.8182(3)
_cell_length_b                   10.8166(7)
_cell_length_c                   21.8043(15)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.65
_cell_volume                     900.38(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.753
_diffrn_reflns_theta_min         1.868
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0317P)²+0.8330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1376
_reflns_number_total             1709
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5326sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        900.37(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239840
_cod_database_fobs_code          2239840
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
S S1 0.5670(2) 0.33458(7) 0.36148(3) 0.0316(2) Uani d 1
C C2 0.4389(8) 0.4860(3) 0.33723(13) 0.0297(7) Uani d 1
N N3 0.5448(8) 0.5631(3) 0.38116(12) 0.0327(7) Uani d 1
H H3 0.487(9) 0.631(3) 0.3829(14) 0.030(10) Uiso d 1
N N4 0.7091(7) 0.5177(2) 0.43328(11) 0.0301(6) Uani d 1
C C5 0.7362(8) 0.3992(3) 0.42932(13) 0.0259(7) Uani d 1
O O6 0.2779(7) 0.5107(2) 0.28964(10) 0.0454(6) Uani d 1
N N7 0.8708(8) 0.3270(3) 0.47486(13) 0.0349(7) Uani d 1
H H7A 0.968(9) 0.259(3) 0.4641(14) 0.035(10) Uiso d 1
H H7B 0.983(10) 0.364(3) 0.5033(17) 0.049(11) Uiso d 1
S S8 0.0629(2) 1.02405(7) 0.34352(4) 0.0334(2) Uani d 1
C C9 0.2461(8) 1.0171(3) 0.41853(13) 0.0294(7) Uani d 1
N N10 0.3361(7) 0.9003(2) 0.42943(12) 0.0315(6) Uani d 1
H H10 0.438(8) 0.884(3) 0.4630(14) 0.024(8) Uiso d 1
N N11 0.2747(8) 0.8126(2) 0.38422(11) 0.0359(7) Uani d 1
C C12 0.1325(8) 0.8645(3) 0.33686(13) 0.0296(7) Uani d 1
O O13 0.2843(7) 1.1052(2) 0.45367(10) 0.0458(7) Uani d 1
N N14 0.0397(10) 0.8045(4) 0.28504(14) 0.0502(9) Uani d 1
H H14A -0.052(11) 0.853(4) 0.2546(19) 0.068(13) Uiso d 1
H H14B 0.074(10) 0.738(4) 0.2852(17) 0.043(12) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C5 S1 C2 88.81(14)
O6 C2 N3 127.9(3)
O6 C2 S1 125.5(2)
N3 C2 S1 106.5(2)
C2 N3 N4 120.0(3)
C2 N3 H3 123(2)
N4 N3 H3 115(2)
C5 N4 N3 109.5(2)
N4 C5 N7 123.6(3)
N4 C5 S1 115.1(2)
N7 C5 S1 121.2(2)
C5 N7 H7A 117(2)
C5 N7 H7B 116(2)
H7A N7 H7B 113(3)
C12 S8 C9 88.66(14)
O13 C9 N10 126.7(3)
O13 C9 S8 125.7(2)
N10 C9 S8 107.6(2)
C9 N10 N11 118.9(3)
C9 N10 H10 118(2)
N11 N10 H10 123(2)
C12 N11 N10 109.6(2)
N11 C12 N14 124.4(3)
N11 C12 S8 115.2(2)
N14 C12 S8 120.4(3)
C12 N14 H14A 115(3)
C12 N14 H14B 115(3)
H14A N14 H14B 130(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.749(3)
S1 C2 1.786(3)
C2 O6 1.226(4)
C2 N3 1.328(4)
N3 N4 1.379(3)
N3 H3 0.77(3)
N4 C5 1.289(4)
C5 N7 1.357(4)
N7 H7A 0.86(3)
N7 H7B 0.85(4)
S8 C12 1.753(3)
S8 C9 1.769(3)
C9 O13 1.230(3)
C9 N10 1.329(4)
N10 N11 1.385(3)
N10 H10 0.84(3)
N11 C12 1.287(4)
C12 N14 1.345(4)
N14 H14A 0.91(4)
N14 H14B 0.73(4)
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
N3 H3 N11 . 0.77(3) 2.12(3) 2.891(4) 174(3)
N7 H7A O13 1_645 0.86(3) 2.07(4) 2.913(4) 167(3)
N7 H7B N4 3_766 0.85(4) 2.21(4) 3.048(4) 171(3)
N10 H10 O13 3_676 0.84(3) 2.09(3) 2.910(3) 165(3)
N14 H14A O6 2 0.91(4) 2.14(4) 3.005(4) 159(4)
N14 H14B O6 . 0.73(4) 2.58(4) 3.306(5) 173(4)
