#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208454.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_2208454
loop_
_publ_author_name
'Wawrzycka-Gorczyca, Irena'
'Siwek, Agata'
'Dobosz, Maria'
_publ_section_title
4-Methyl-N-(4-oxo-2-thioxoimidazolidin-3-yl)-1,2,3-thiadiazole-5-carboxamide
_journal_coeditor_code           WN6416
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o864
_journal_page_last               o865
_journal_paper_doi               10.1107/S1600536806003369
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H7 N5 O2 S2'
_chemical_formula_moiety         'C7 H7 N5 O2 S2'
_chemical_formula_sum            'C7 H7 N5 O2 S2'
_chemical_formula_weight         257.30
_chemical_name_systematic
;
4-Methyl-N-(4-oxo-2-thioxoimidazolidin-3-yl)-1,2,3-thiadiazole-5-carboxamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.74(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.528(2)
_cell_length_b                   7.2390(10)
_cell_length_c                   19.843(4)
_cell_measurement_reflns_used    66
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      6
_cell_volume                     1080.8(4)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1991)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2227
_diffrn_reflns_theta_full        75.07
_diffrn_reflns_theta_max         75.07
_diffrn_reflns_theta_min         5.88
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.458
_exptl_absorpt_correction_T_max  0.1353
_exptl_absorpt_correction_T_min  0.0349
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '(Dwiggins, 1975)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.462
_refine_ls_extinction_coef       0.0078(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0545
_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)+(0.1205P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1514
_reflns_number_gt                1640
_reflns_number_total             2184
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wn6416.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
S1 0.40296(8) 0.88715(11) 0.23310(3) 0.0589(3) Uani d . 1 S
S2 0.16190(10) 0.77031(10) 0.52810(4) 0.0611(3) Uani d . 1 S
N1 0.1102(3) 1.0270(3) 0.21317(10) 0.0529(5) Uani d . 1 N
N2 0.2606(3) 1.0047(4) 0.18480(10) 0.0617(6) Uani d . 1 N
N3 0.1770(3) 0.6448(3) 0.37863(9) 0.0486(5) Uani d . 1 N
H3N 0.0654 0.6187 0.3537 0.058 Uiso d R 1 H
N4 0.2197(3) 0.5225(3) 0.42979(9) 0.0453(4) Uani d . 1 N
N5 0.2779(3) 0.4195(3) 0.53043(10) 0.0510(5) Uani d . 1 N
H5N 0.3114 0.3946 0.5782 0.061 Uiso d R 1 H
O1 0.4569(2) 0.7610(3) 0.38045(10) 0.0641(5) Uani d . 1 O
O2 0.2900(3) 0.2754(3) 0.36300(10) 0.0680(6) Uani d . 1 O
C3 0.2570(3) 0.8608(3) 0.29453(10) 0.0415(4) Uani d . 1 C
C4 0.1011(3) 0.9481(3) 0.27579(11) 0.0438(5) Uani d . 1 C
C5 -0.0622(4) 0.9758(4) 0.31469(15) 0.0622(7) Uani d . 1 C
H5A -0.0777 1.1051 0.3235 0.075 Uiso calc R 1 H
H5B -0.0512 0.9101 0.3566 0.075 Uiso calc R 1 H
H5C -0.1631 0.9301 0.2891 0.075 Uiso calc R 1 H
C6 0.3095(3) 0.7533(3) 0.35556(11) 0.0434(5) Uani d . 1 C
C7 0.2779(3) 0.3437(3) 0.41777(12) 0.0478(5) Uani d . 1 C
C8 0.3167(3) 0.2659(3) 0.48672(13) 0.0524(6) Uani d . 1 C
H8A 0.2409 0.1609 0.4957 0.063 Uiso calc R 1 H
H8B 0.4401 0.2283 0.4919 0.063 Uiso calc R 1 H
C9 0.2204(3) 0.5691(3) 0.49736(11) 0.0428(5) Uani d . 1 C
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
S1 0.0498(4) 0.0765(5) 0.0508(4) -0.0032(3) 0.0062(2) 0.0138(3)
S2 0.0672(5) 0.0522(4) 0.0644(4) -0.0014(3) 0.0091(3) -0.0118(3)
N1 0.0653(12) 0.0492(11) 0.0435(10) -0.0006(9) -0.0104(8) 0.0081(8)
N2 0.0722(13) 0.0692(14) 0.0436(11) -0.0072(11) -0.0019(9) 0.0143(9)
N3 0.0542(10) 0.0504(10) 0.0404(9) -0.0057(8) -0.0114(7) 0.0120(8)
N4 0.0560(10) 0.0436(9) 0.0359(8) 0.0009(8) -0.0053(7) 0.0067(7)
N5 0.0580(11) 0.0525(10) 0.0420(9) 0.0007(9) -0.0071(8) 0.0066(8)
O1 0.0452(9) 0.0848(14) 0.0615(11) -0.0001(8) -0.0121(8) 0.0212(9)
O2 0.0859(14) 0.0650(11) 0.0533(10) 0.0002(10) 0.0075(9) -0.0161(8)
C3 0.0445(10) 0.0451(10) 0.0348(9) -0.0027(8) -0.0025(7) 0.0018(8)
C4 0.0519(12) 0.0390(10) 0.0398(10) 0.0008(8) -0.0081(8) 0.0010(8)
C5 0.0636(15) 0.0564(15) 0.0667(16) 0.0172(12) 0.0058(12) 0.0053(12)
C6 0.0441(11) 0.0468(11) 0.0389(10) 0.0035(8) -0.0036(8) 0.0031(8)
C7 0.0476(11) 0.0457(11) 0.0501(11) -0.0031(9) 0.0022(9) -0.0020(9)
C8 0.0522(12) 0.0468(12) 0.0575(14) 0.0014(9) -0.0062(10) 0.0060(9)
C9 0.0408(9) 0.0478(10) 0.0395(10) -0.0065(8) -0.0019(7) 0.0013(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
N2 S1 C3 93.02(11) no
N2 N1 C4 114.3(2) no
N1 N2 S1 111.94(16) no
C6 N3 N4 117.48(18) no
C6 N3 H3N 124.6 no
N4 N3 H3N 115.2 no
N3 N4 C9 123.5(2) no
N3 N4 C7 122.68(19) no
C9 N4 C7 113.69(18) no
C9 N5 C8 113.49(19) no
C9 N5 H5N 133.6 no
C8 N5 H5N 112.6 no
C4 C3 C6 131.8(2) no
C4 C3 S1 108.90(15) no
C6 C3 S1 119.30(16) no
N1 C4 C3 111.8(2) no
N1 C4 C5 118.7(2) no
C3 C4 C5 129.4(2) no
C4 C5 H5A 109.5 no
C4 C5 H5B 109.5 no
H5A C5 H5B 109.5 no
C4 C5 H5C 109.5 no
H5A C5 H5C 109.5 no
H5B C5 H5C 109.5 no
O1 C6 N3 124.5(2) no
O1 C6 C3 122.1(2) no
N3 C6 C3 113.44(19) no
O2 C7 N4 124.9(2) no
O2 C7 C8 130.8(3) no
N4 C7 C8 104.3(2) no
N5 C8 C7 102.75(19) no
N5 C8 H8A 111.2 no
C7 C8 H8A 111.2 no
N5 C8 H8B 111.2 no
C7 C8 H8B 111.2 no
H8A C8 H8B 109.1 no
N5 C9 N4 105.7(2) no
N5 C9 S2 128.63(18) no
N4 C9 S2 125.63(17) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 N2 1.652(2) yes
S1 C3 1.676(2) yes
S2 C9 1.644(2) yes
N1 N2 1.290(3) yes
N1 C4 1.371(3) yes
N3 C6 1.360(3) no
N3 N4 1.378(2) yes
N3 H3N 0.9799 no
N4 C9 1.382(3) yes
N4 C7 1.389(3) yes
N5 C9 1.332(3) yes
N5 C8 1.446(3) yes
N5 H5N 0.9900 no
O1 C6 1.202(3) no
O2 C7 1.200(3) yes
C3 C4 1.374(3) yes
C3 C6 1.483(3) no
C4 C5 1.485(3) no
C5 H5A 0.9600 no
C5 H5B 0.9600 no
C5 H5C 0.9600 no
C7 C8 1.500(3) yes
C8 H8A 0.9700 no
C8 H8B 0.9700 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 H3N N1 2_545 0.98 1.96 2.912(3) 163 yes
N5 H5N O1 3_666 0.99 2.21 2.933(3) 129 yes
N5 H5N N2 4_576 0.99 2.28 3.118(3) 142 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 N1 N2 S1 -0.5(3) no
C3 S1 N2 N1 0.9(2) no
C6 N3 N4 C9 86.1(3) no
C6 N3 N4 C7 -89.4(3) no
N2 S1 C3 C4 -1.04(17) no
N2 S1 C3 C6 178.12(19) no
N2 N1 C4 C3 -0.3(3) no
N2 N1 C4 C5 176.2(2) no
C6 C3 C4 N1 -178.1(2) no
S1 C3 C4 N1 0.9(2) no
C6 C3 C4 C5 6.0(4) no
S1 C3 C4 C5 -175.0(2) no
N4 N3 C6 O1 -6.7(4) no
N4 N3 C6 C3 171.90(19) no
C4 C3 C6 O1 -143.2(3) no
S1 C3 C6 O1 37.9(3) no
C4 C3 C6 N3 38.2(3) no
S1 C3 C6 N3 -140.75(19) no
N3 N4 C7 O2 -3.1(4) no
C9 N4 C7 O2 -179.1(2) no
N3 N4 C7 C8 177.3(2) no
C9 N4 C7 C8 1.3(2) no
C9 N5 C8 C7 1.3(3) no
O2 C7 C8 N5 179.0(3) no
N4 C7 C8 N5 -1.5(2) no
C8 N5 C9 N4 -0.5(3) no
C8 N5 C9 S2 179.74(17) no
N3 N4 C9 N5 -176.5(2) no
C7 N4 C9 N5 -0.5(3) no
N3 N4 C9 S2 3.3(3) no
C7 N4 C9 S2 179.19(17) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126303
