#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/26/2212612.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_2212612
loop_
_publ_author_name
'Hökelek, Tuncer'
'Seferoğlu, Zeynel'
'Şahin, Ertan'
'Ertan, Nermin'
_publ_section_title
5-[(5-Methylthiazol-2-yl)diazenyl]pyrimidine-2,4,6(1H,3H,5H)-trione
_journal_coeditor_code           IM2004
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1506
_journal_page_last               o1508
_journal_paper_doi               10.1107/S1600536807009051
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 N5 O3 S'
_chemical_formula_moiety         'C8 H7 N5 O3 S'
_chemical_formula_sum            'C8 H7 N5 O3 S'
_chemical_formula_weight         253.24
_chemical_name_systematic
;
5-[(5-Methylthiazol-2-yl)diazenyl]pyrimidine-2,4,6(1H,3H,5H)-trione
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.321(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.092(2)
_cell_length_b                   7.0989(9)
_cell_length_c                   12.913(2)
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.5407
_cell_measurement_theta_min      2.9696
_cell_volume                     1075.7(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28688
_diffrn_reflns_theta_full        30.66
_diffrn_reflns_theta_max         30.66
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.544
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.1064
_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)+(0.1678P)²+0.1113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3017
_refine_ls_wR_factor_ref         0.3406
_reflns_number_gt                2154
_reflns_number_total             3294
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212612
_cod_database_fobs_code          2212612
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_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 0.37726(9) 0.23263(15) 0.03524(8) 0.0671(4) Uani d . 1
O O1 0.2817(3) -0.3123(5) -0.2114(3) 0.0797(9) Uani d . 1
O O2 0.0564(3) -0.7936(4) -0.2091(3) 0.0770(9) Uani d . 1
O O3 0.0793(3) -0.2922(4) 0.0151(3) 0.0725(8) Uani d . 1
N N1 0.2537(3) 0.2369(4) 0.1443(3) 0.0625(8) Uani d . 1
N N2 0.2224(3) -0.0299(5) 0.0301(3) 0.0616(8) Uani d . 1
N N3 0.2420(3) -0.1211(4) -0.0487(3) 0.0583(7) Uani d . 1
N N4 0.1665(3) -0.5484(5) -0.2112(3) 0.0612(8) Uani d D 1
H H41 0.192(4) -0.609(6) -0.253(3) 0.079(13) Uiso d D 1
N N5 0.0725(3) -0.5440(4) -0.0942(3) 0.0586(8) Uani d D 1
H H51 0.025(3) -0.602(5) -0.075(4) 0.085(15) Uiso d D 1
C C1 0.2765(3) 0.1377(6) 0.0721(3) 0.0588(9) Uani d . 1
C C2 0.3170(3) 0.4032(5) 0.1712(3) 0.0649(9) Uani d . 1
H H2 0.3107 0.4934 0.2204 0.078 Uiso calc R 1
C C3 0.3879(3) 0.4254(5) 0.1217(3) 0.0653(10) Uani d . 1
C C4 0.1908(3) -0.2806(5) -0.0883(3) 0.0552(8) Uani d . 1
H H4 0.1278 -0.2138 -0.1503 0.066 Uiso calc R 1
C C5 0.2180(3) -0.3760(5) -0.1750(3) 0.0583(9) Uani d . 1
C C6 0.0960(3) -0.6400(6) -0.1750(3) 0.0600(9) Uani d . 1
C C7 0.1099(3) -0.3692(6) -0.0524(3) 0.0598(9) Uani d . 1
C C8 0.4671(4) 0.5860(6) 0.1347(4) 0.0826(13) Uani d . 1
H H8A 0.4532 0.6865 0.1765 0.124 Uiso calc R 1
H H8B 0.4543 0.6303 0.0596 0.124 Uiso calc R 1
H H8C 0.5445 0.5440 0.1762 0.124 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C1 S1 C3 89.03(18)
C1 N1 C2 109.6(3)
N3 N2 C1 119.2(3)
C4 N3 N2 119.1(3)
C6 N4 C5 127.6(3)
C6 N4 H41 119(3)
C5 N4 H41 113(3)
C7 N5 C6 125.9(3)
C7 N5 H51 120(3)
C6 N5 H51 114(3)
N1 C1 N2 120.7(3)
N1 C1 S1 115.6(3)
N2 C1 S1 123.7(3)
C3 C2 N1 116.0(3)
C3 C2 H2 122.0
N1 C2 H2 122.0
C2 C3 C8 128.5(4)
C2 C3 S1 109.8(3)
C8 C3 S1 121.8(3)
N3 C4 C7 124.5(3)
N3 C4 C5 116.2(3)
C7 C4 C5 119.4(3)
N3 C4 H4 90.0
C7 C4 H4 90.0
C5 C4 H4 90.0
O1 C5 N4 121.3(3)
O1 C5 C4 124.1(4)
N4 C5 C4 114.7(3)
O2 C6 N4 123.5(3)
O2 C6 N5 121.0(3)
N4 C6 N5 115.5(3)
O3 C7 N5 120.8(3)
O3 C7 C4 122.4(4)
N5 C7 C4 116.7(3)
C3 C8 H8A 109.5
C3 C8 H8B 109.5
H8A C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.726(4)
S1 C3 1.732(4)
O3 C7 1.237(4)
N1 C1 1.304(5)
N1 C2 1.395(5)
N2 N3 1.324(4)
N2 C1 1.368(5)
N4 C6 1.369(5)
N4 C5 1.376(5)
N4 H41 0.87(5)
N5 C7 1.355(5)
N5 C6 1.390(5)
N5 H51 0.87(4)
C2 H2 0.9300
C3 C2 1.350(5)
C3 C8 1.500(6)
C4 N3 1.299(5)
C4 C7 1.473(5)
C4 C5 1.481(5)
C4 H4 0.9800
C5 O1 1.211(4)
C6 O2 1.204(5)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
N4 H41 N1 4 0.87(5) 2.05(5) 2.910(5) 177(4) yes
N5 H51 O3 3_545 0.87(4) 1.99(4) 2.853(6) 172(3) 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
C3 S1 C1 N1 -1.3(3)
C3 S1 C1 N2 178.6(3)
C1 S1 C3 C2 0.5(3)
C1 S1 C3 C8 -179.9(4)
C2 N1 C1 N2 -178.2(3)
C2 N1 C1 S1 1.8(4)
C1 N1 C2 C3 -1.4(5)
N3 N2 C1 N1 175.6(3)
N3 N2 C1 S1 -4.3(5)
C1 N2 N3 C4 179.8(3)
C6 N4 C5 O1 177.7(4)
C6 N4 C5 C4 -1.1(6)
C5 N4 C6 O2 -178.1(4)
C5 N4 C6 N5 1.6(6)
C7 N5 C6 O2 -178.1(4)
C7 N5 C6 N4 2.2(6)
C6 N5 C7 O3 176.4(4)
C6 N5 C7 C4 -5.8(6)
C8 C3 C2 N1 -179.2(4)
S1 C3 C2 N1 0.4(5)
C7 C4 N3 N2 0.6(6)
C5 C4 N3 N2 -179.2(3)
N3 C4 C5 O1 -1.7(6)
C7 C4 C5 O1 178.5(4)
N3 C4 C5 N4 177.1(3)
C7 C4 C5 N4 -2.7(5)
N3 C4 C7 O3 3.9(6)
C5 C4 C7 O3 -176.3(4)
N3 C4 C7 N5 -174.0(3)
C5 C4 C7 N5 5.9(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655182
