#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/58/2215813.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_2215813
loop_
_publ_author_name
'Kruszynski, Rafal'
'Trzesowska, Agata'
'Przybycin, Magdalena'
'Gil, Kamil'
'Dobosz, Maria'
_publ_section_title
;
 2-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic
 acid
;
_journal_coeditor_code           BT2545
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4378
_journal_page_last               o4378
_journal_paper_doi               10.1107/S1600536807051185
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H7 N3 O2 S'
_chemical_formula_moiety         'C5 H7 N3 O2 S'
_chemical_formula_sum            'C5 H7 N3 O2 S'
_chemical_formula_weight         173.20
_chemical_name_systematic
;
2-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.250(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1706(3)
_cell_length_b                   9.4818(6)
_cell_length_c                   15.6763(9)
_cell_measurement_reflns_used    99
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     758.56(8)
_computing_cell_refinement       'KM-4 Software (Kuma, 1993)'
_computing_data_collection       'KM-4 Software (Kuma, 1993)'
_computing_data_reduction
;
DATAPROC (Gałdecki et al.,  1998)
;
_computing_molecular_graphics
;
XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows
(Version 1.062; Farrugia, 1997)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1354
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        2.12
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                1108
_reflns_number_total             1354
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2545.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215813
_cod_database_fobs_code          2215813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
S S1 0.99527(11) 1.04539(6) 0.63708(3) 0.0393(2) Uani d . 1
O O1 0.7717(3) 0.88549(17) 0.88096(9) 0.0437(4) Uani d . 1
H H1O 0.8832 0.8517 0.9185 0.066 Uiso calc R 1
C C4 0.8051(4) 0.8362(2) 0.80424(12) 0.0301(5) Uani d . 1
O O2 0.9822(3) 0.76167(17) 0.79093(9) 0.0420(4) Uani d . 1
N N1 0.7338(3) 0.8532(2) 0.52587(10) 0.0401(5) Uani d . 1
H H1N 0.8106 0.8759 0.4831 0.048 Uiso calc R 1
N N3 0.6155(3) 0.84909(19) 0.64966(10) 0.0313(4) Uani d . 1
C C3 0.5851(4) 0.8886(2) 0.73708(12) 0.0336(5) Uani d . 1
H H3A 0.4208 0.8508 0.7495 0.040 Uiso calc R 1
H H3B 0.5763 0.9905 0.7407 0.040 Uiso calc R 1
C C2 0.7812(4) 0.9166(2) 0.60293(12) 0.0335(5) Uani d . 1
N N2 0.5497(4) 0.7480(2) 0.52213(11) 0.0413(5) Uani d . 1
C C1 0.4797(4) 0.7476(2) 0.59811(12) 0.0347(5) Uani d . 1
C C5 0.2828(4) 0.6513(3) 0.62525(15) 0.0438(6) Uani d . 1
H H5A 0.2063 0.5947 0.5769 0.066 Uiso calc R 1
H H5B 0.1484 0.7056 0.6456 0.066 Uiso calc R 1
H H5C 0.3661 0.5911 0.6708 0.066 Uiso calc R 1
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 0.0452(3) 0.0464(4) 0.0274(3) -0.0021(3) 0.0090(2) -0.0016(2)
O1 0.0578(10) 0.0515(10) 0.0206(8) 0.0089(8) 0.0029(7) -0.0014(7)
C4 0.0347(11) 0.0345(11) 0.0222(10) -0.0032(9) 0.0082(8) 0.0018(9)
O2 0.0366(8) 0.0546(10) 0.0356(8) 0.0104(8) 0.0087(7) 0.0068(7)
N1 0.0495(11) 0.0521(12) 0.0202(9) -0.0065(10) 0.0095(8) 0.0007(8)
N3 0.0322(9) 0.0425(10) 0.0198(8) 0.0043(8) 0.0065(7) 0.0005(8)
C3 0.0347(11) 0.0459(13) 0.0212(10) 0.0065(10) 0.0073(8) -0.0003(9)
C2 0.0339(11) 0.0451(13) 0.0216(10) 0.0079(10) 0.0049(8) 0.0022(9)
N2 0.0481(11) 0.0523(12) 0.0231(9) -0.0059(10) 0.0042(8) -0.0024(8)
C1 0.0366(11) 0.0445(13) 0.0220(10) 0.0046(10) 0.0015(8) 0.0012(9)
C5 0.0442(13) 0.0501(14) 0.0375(13) -0.0011(11) 0.0077(10) 0.0021(11)
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 0.0000 0.0000 '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 0.0060 '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
_geom_angle_publ_flag
C4 O1 H1O 109.5 no
O2 C4 O1 125.34(19) no
O2 C4 C3 125.76(18) no
O1 C4 C3 108.89(17) no
C2 N1 N2 112.98(17) no
C2 N1 H1N 123.5 no
N2 N1 H1N 123.5 no
C2 N3 C1 108.44(16) no
C2 N3 C3 123.71(18) no
C1 N3 C3 127.75(17) no
N3 C3 C4 112.98(16) no
N3 C3 H3A 109.0 no
C4 C3 H3A 109.0 no
N3 C3 H3B 109.0 no
C4 C3 H3B 109.0 no
H3A C3 H3B 107.8 no
N1 C2 N3 103.51(18) no
N1 C2 S1 129.18(17) no
N3 C2 S1 127.30(15) no
C1 N2 N1 104.81(17) no
N2 C1 N3 110.26(19) no
N2 C1 C5 124.8(2) no
N3 C1 C5 124.95(18) no
C1 C5 H5A 109.5 no
C1 C5 H5B 109.5 no
H5A C5 H5B 109.5 no
C1 C5 H5C 109.5 no
H5A C5 H5C 109.5 no
H5B C5 H5C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.677(2) no
O1 C4 1.327(2) no
O1 H1O 0.8200 no
C4 O2 1.201(2) no
C4 C3 1.505(3) no
N1 C2 1.336(3) no
N1 N2 1.374(3) no
N1 H1N 0.8600 no
N3 C2 1.372(3) no
N3 C1 1.374(3) no
N3 C3 1.453(2) no
C3 H3A 0.9700 no
C3 H3B 0.9700 no
N2 C1 1.299(3) no
C1 C5 1.480(3) no
C5 H5A 0.9600 no
C5 H5B 0.9600 no
C5 H5C 0.9600 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
O1 H1O N2 4_676 0.82 1.96 2.746(2) 161.8
N1 H1N S1 3_776 0.86 2.39 3.2499(18) 175.8
C3 H3A O2 1_455 0.97 2.60 3.567(2) 176.2
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
N3 C3 C4 O1 175.46(17) no
N3 C3 C4 O2 -4.6(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16497999
