#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/59/2205905.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_2205905
loop_
_publ_author_name
'Hartung, Jens'
'Daniel, Kristina'
'Gottwald, Thomas'
'Svoboda, Ingrid'
'Fuess, Hartmut'
_publ_section_title
;
 N-Hydroxy-4,5-dimethylthiazole-2(3H)-thione hemihydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1741
_journal_page_last               o1743
_journal_paper_doi               10.1107/S1600536805013851
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C5 H7 N1 O1 S2 , 0.5H2 O'
_chemical_formula_moiety         'C5 H7 N1 O1 S2 , 0.5H2 O'
_chemical_formula_sum            'C5 H8 N O1.5 S2'
_chemical_formula_weight         170.24
_chemical_melting_point          361
_chemical_name_systematic
;
N-Hydroxy-4,5-dimethylthiazole-2(3H)-thione hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.08(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.5640(10)
_cell_length_b                   4.141(2)
_cell_length_c                   15.000(2)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      18.634
_cell_measurement_theta_min      2.854
_cell_volume                     1546.7(8)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2002)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics
'PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997, 2005)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur with Sapphire CCD area-detector'
_diffrn_measurement_method       'Rotation method data acquisition using ω'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4701
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.8082
_exptl_absorpt_correction_T_min  0.7081
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlisRED (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.066P)²+1.7712P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1405
_reflns_number_total             1553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6486.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C5 H8 N1 O1.5 S2'
_cod_database_code               2205905
_cod_database_fobs_code          2205905
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C2 0.87502(9) 0.3732(5) -0.23171(14) 0.0329(5) Uani d . 1 C
C4 0.88961(9) 0.1224(5) -0.08652(14) 0.0342(5) Uani d . 1 C
C5 0.83604(9) 0.0921(6) -0.11154(16) 0.0396(5) Uani d . 1 C
C6 0.92764(11) 0.0117(7) -0.00164(16) 0.0468(6) Uani d . 1 C
H6A 0.9471 0.1938 0.0289 0.056 Uiso calc R 1 H
H6B 0.9524 -0.1406 -0.0172 0.056 Uiso calc R 1 H
H6C 0.9079 -0.0894 0.0382 0.056 Uiso calc R 1 H
C7 0.79860(11) -0.0493(7) -0.0580(2) 0.0558(7) Uani d . 1 C
H7A 0.7792 -0.2263 -0.0915 0.067 Uiso calc R 1 H
H7B 0.7737 0.1131 -0.0482 0.067 Uiso calc R 1 H
H7C 0.8189 -0.1253 0.0000 0.067 Uiso calc R 1 H
O1 0.96375(6) 0.3586(4) -0.13833(11) 0.0403(4) Uani d . 1 O
H1 0.9769(11) 0.231(6) -0.1728(19) 0.048 Uiso d . 1 H
O2 1.0000 0.9535(6) -0.2500 0.0414(5) Uani d SD 1 O
H2 0.9731(8) 0.835(6) -0.2692(19) 0.050 Uiso d D 1 H
N3 0.91002(7) 0.2788(4) -0.15462(12) 0.0317(4) Uani d . 1 N
S1 0.81192(2) 0.25397(15) -0.22096(4) 0.0439(2) Uani d . 1 S
S2 0.88807(3) 0.56562(15) -0.32230(4) 0.0441(2) Uani d . 1 S
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
C2 0.0339(10) 0.0332(10) 0.0327(10) 0.0009(8) 0.0096(8) -0.0033(8)
C4 0.0410(12) 0.0364(11) 0.0290(10) 0.0023(9) 0.0161(9) -0.0019(8)
C5 0.0401(12) 0.0437(13) 0.0393(12) -0.0008(10) 0.0179(9) -0.0027(10)
C6 0.0535(14) 0.0566(14) 0.0313(11) 0.0031(12) 0.0116(10) 0.0064(11)
C7 0.0524(15) 0.0645(17) 0.0606(16) -0.0093(13) 0.0341(13) -0.0033(14)
O1 0.0300(8) 0.0554(10) 0.0365(8) -0.0038(7) 0.0098(6) -0.0054(7)
O2 0.0337(12) 0.0449(13) 0.0486(13) 0.000 0.0158(10) 0.000
N3 0.0292(9) 0.0383(10) 0.0296(9) -0.0005(7) 0.0108(7) -0.0018(7)
S1 0.0308(3) 0.0542(4) 0.0462(4) -0.0002(2) 0.0076(2) 0.0020(3)
S2 0.0521(4) 0.0487(4) 0.0314(3) -0.0051(3) 0.0090(3) 0.0052(2)
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'
O O 0.0106 0.0060 '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'
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
N3 C2 S2 128.21(16) ?
N3 C2 S1 106.80(15) yes
S2 C2 S1 124.99(13) yes
C5 C4 N3 111.29(19) yes
C5 C4 C6 129.7(2) ?
N3 C4 C6 119.0(2) yes
C4 C5 C7 128.4(2) yes
C4 C5 S1 110.31(16) yes
C7 C5 S1 121.3(2) ?
C4 C6 H6A 109.5 ?
C4 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C4 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C5 C7 H7A 109.5 ?
C5 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C5 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N3 O1 H1 104.9(19) yes
C2 N3 O1 121.50(17) ?
C2 N3 C4 118.22(18) yes
O1 N3 C4 120.00(17) ?
C2 S1 C5 93.36(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N3 1.350(3) ?
C2 S2 1.673(2) ?
C2 S1 1.729(2) ?
C4 C5 1.341(3) yes
C4 N3 1.406(3) ?
C4 C6 1.489(3) yes
C5 C7 1.501(3) yes
C5 S1 1.751(2) ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
O1 N3 1.380(2) ?
O1 H1 0.86(3) ?
O2 H2 0.841(10) ?
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 H1 O2 1_545 0.86(3) 1.82(3) 2.680(2) 176(3)
O2 H2 S2 . 0.841(10) 2.412(11) 3.2463(15) 171(3)
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
N3 C4 C5 C7 -177.8(2)
C6 C4 C5 C7 3.5(4)
N3 C4 C5 S1 1.0(2)
C6 C4 C5 S1 -177.8(2)
S2 C2 N3 O1 5.3(3)
S1 C2 N3 O1 -175.14(15)
S2 C2 N3 C4 179.29(16)
S1 C2 N3 C4 -1.2(2)
C5 C4 N3 C2 0.2(3)
C6 C4 N3 C2 179.0(2)
C5 C4 N3 O1 174.21(18)
C6 C4 N3 O1 -6.9(3)
N3 C2 S1 C5 1.41(16)
S2 C2 S1 C5 -179.03(15)
C4 C5 S1 C2 -1.40(18)
C7 C5 S1 C2 177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129473
