#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/76/2207656.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_2207656
loop_
_publ_author_name
'Ying-Hui Ren'
'Ji-Rong Song'
'Jie Huang'
'Xiao-Hong Sun'
'Huai-Ming Hu'
_publ_section_title
;
 Methyl
 N-[4-(4,6-dimethylpyrimidin-2-ylamino)thiocarbonyl]carbamate
;
_journal_coeditor_code           SU6229
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4013
_journal_page_last               o4015
_journal_paper_doi               10.1107/S160053680503549X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H12 N4 O2 S'
_chemical_formula_moiety         'C9 H12 N4 O2 S'
_chemical_formula_sum            'C9 H12 N4 O2 S'
_chemical_formula_weight         240.29
_chemical_name_systematic
;
Methyl N-[4-(4,6-dimethylpyrimidin-2-ylamino)thiocarbonyl]carbamate
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 118.557(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.537(5)
_cell_length_b                   6.759(2)
_cell_length_c                   11.148(3)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.64
_cell_volume                     1160.6(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2964
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0389
_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)+(0.0829P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                873
_reflns_number_total             1117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6229.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1160.5(6)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               2207656
_cod_database_fobs_code          2207656
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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 0.42358(5) 0.0000 0.28149(7) 0.0684(3) Uani d S 1 S
N1 0.36437(14) 0.0000 0.6602(2) 0.0537(5) Uani d S 1 N
N2 0.23026(13) 0.0000 0.4527(2) 0.0506(5) Uani d S 1 N
N3 0.36658(15) 0.0000 0.4587(2) 0.0529(6) Uani d S 1 N
N4 0.25798(14) 0.0000 0.2360(2) 0.0562(6) Uani d S 1 N
O1 0.24719(18) 0.0000 0.0222(2) 0.1142(10) Uani d S 1 O
O2 0.13102(14) 0.0000 0.05291(19) 0.0705(6) Uani d S 1 O
C1 0.3750(3) 0.0000 0.8824(3) 0.0769(9) Uani d S 1 C
C2 0.32075(19) 0.0000 0.7309(3) 0.0557(6) Uani d S 1 C
C3 0.23133(19) 0.0000 0.6655(3) 0.0593(7) Uani d S 1 C
C4 0.18634(17) 0.0000 0.5252(3) 0.0542(6) Uani d S 1 C
C5 0.0897(2) 0.0000 0.4438(4) 0.0730(8) Uani d S 1 C
C6 0.31628(16) 0.0000 0.5246(2) 0.0466(6) Uani d S 1 C
C7 0.34475(17) 0.0000 0.3232(3) 0.0499(6) Uani d S 1 C
C8 0.2158(2) 0.0000 0.0947(3) 0.0624(7) Uani d S 1 C
C9 0.0754(3) 0.0000 -0.0931(3) 0.0882(11) Uani d S 1 C
H3 0.419(3) 0.0000 0.518(4) 0.080 Uiso d S 1 H
H4 0.223(2) 0.0000 0.273(4) 0.080 Uiso d S 1 H
H3A 0.201(2) 0.0000 0.711(4) 0.080 Uiso d S 1 H
H1B 0.343(2) 0.0000 0.928(3) 0.080 Uiso d S 1 H
H1A 0.4056(16) 0.101(3) 0.917(2) 0.080 Uiso d . 1 H
H5A 0.068(3) 0.0000 0.497(3) 0.080 Uiso d S 1 H
H5B 0.0707(14) 0.116(4) 0.387(2) 0.080 Uiso d . 1 H
H9A 0.018(3) 0.0000 -0.103(3) 0.080 Uiso d S 1 H
H9B 0.0895(15) 0.106(3) -0.132(2) 0.080 Uiso d . 1 H
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 0.0488(5) 0.1060(6) 0.0616(5) 0.000 0.0353(4) 0.000
N1 0.0417(12) 0.0686(13) 0.0538(12) 0.000 0.0251(10) 0.000
N2 0.0379(12) 0.0628(13) 0.0554(12) 0.000 0.0258(10) 0.000
N3 0.0341(11) 0.0750(14) 0.0530(12) 0.000 0.0236(10) 0.000
N4 0.0448(13) 0.0778(15) 0.0501(13) 0.000 0.0261(11) 0.000
O1 0.0714(15) 0.222(3) 0.0577(14) 0.000 0.0378(12) 0.000
O2 0.0507(11) 0.1025(15) 0.0506(11) 0.000 0.0180(9) 0.000
C1 0.066(2) 0.111(3) 0.0542(18) 0.000 0.0291(17) 0.000
C2 0.0570(16) 0.0634(16) 0.0554(15) 0.000 0.0339(13) 0.000
C3 0.0513(16) 0.0737(17) 0.0675(18) 0.000 0.0402(14) 0.000
C4 0.0405(13) 0.0614(15) 0.0668(17) 0.000 0.0306(13) 0.000
C5 0.0412(16) 0.096(2) 0.087(2) 0.000 0.0355(16) 0.000
C6 0.0387(13) 0.0541(14) 0.0512(14) 0.000 0.0248(11) 0.000
C7 0.0452(15) 0.0556(14) 0.0517(14) 0.000 0.0255(12) 0.000
C8 0.0521(17) 0.0798(19) 0.0561(16) 0.000 0.0265(14) 0.000
C9 0.071(2) 0.125(3) 0.0521(18) 0.000 0.0167(17) 0.000
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'
S S 0.1246 0.1234 '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'
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
C6 N1 C2 116.0(2) y
C6 N2 C4 116.4(2) y
C7 N3 C6 132.0(2) y
C7 N3 H3 119(2) ?
C6 N3 H3 109(2) ?
C7 N4 C8 128.4(2) y
C7 N4 H4 117(2) ?
C8 N4 H4 115(2) ?
C8 O2 C9 115.8(3) y
C2 C1 H1B 114(2) ?
C2 C1 H1A 115.9(17) ?
H1B C1 H1A 100(2) ?
N1 C2 C3 121.0(2) y
N1 C2 C1 115.7(3) y
C3 C2 C1 123.2(3) y
C4 C3 C2 119.4(2) y
C4 C3 H3A 118(2) ?
C2 C3 H3A 122(2) ?
N2 C4 C3 119.8(2) y
N2 C4 C5 116.2(3) y
C3 C4 C5 124.0(3) y
C4 C5 H5A 110(3) ?
C4 C5 H5B 109.7(13) ?
H5A C5 H5B 109.1(18) ?
N2 C6 N1 127.2(2) y
N2 C6 N3 120.3(2) y
N1 C6 N3 112.4(2) y
N4 C7 N3 114.6(2) y
N4 C7 S1 126.81(19) y
N3 C7 S1 118.6(2) y
O1 C8 O2 124.9(3) y
O1 C8 N4 127.7(3) y
O2 C8 N4 107.4(2) y
O2 C9 H9A 104(2) ?
O2 C9 H9B 109.8(15) ?
H9A C9 H9B 116.2(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.656(3) y
N1 C6 1.333(3) y
N1 C2 1.336(3) y
N2 C6 1.327(3) y
N2 C4 1.357(3) y
N3 C7 1.370(3) y
N3 C6 1.392(3) y
N3 H3 0.84(4) ?
N4 C7 1.359(3) y
N4 C8 1.383(3) y
N4 H4 0.88(4) ?
O1 C8 1.176(3) y
O2 C8 1.329(4) y
O2 C9 1.443(4) y
C1 C2 1.490(4) y
C1 H1B 0.91(3) ?
C1 H1A 0.84(2) ?
C2 C3 1.378(4) y
C3 C4 1.375(4) y
C3 H3A 0.89(3) ?
C4 C5 1.492(4) y
C5 H5A 0.85(3) ?
C5 H5B 0.96(2) ?
C9 H9A 0.96(4) ?
C9 H9B 0.93(2) ?
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 S1 5_656 0.84(4) 2.59(4) 3.426(2) 174(3)
N4 H4 N2 . 0.88(4) 1.95(4) 2.683(3) 140(3)
C1 H1B O1 1_556 0.91(3) 2.37(4) 3.284(5) 174(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
C6 N1 C2 C3 0.0000(10)
C6 N1 C2 C1 180.0000(10)
N1 C2 C3 C4 0.0000(10)
C1 C2 C3 C4 180.0000(10)
C6 N2 C4 C3 0.0
C6 N2 C4 C5 180.0
C2 C3 C4 N2 0.0000(10)
C2 C3 C4 C5 180.0000(10)
C4 N2 C6 N1 0.0
C4 N2 C6 N3 180.0
C2 N1 C6 N2 0.0
C2 N1 C6 N3 180.0
C7 N3 C6 N2 0.0
C7 N3 C6 N1 180.0
C8 N4 C7 N3 180.0
C8 N4 C7 S1 0.0
C6 N3 C7 N4 0.0
C6 N3 C7 S1 180.0
C9 O2 C8 O1 0.0
C9 O2 C8 N4 180.0
C7 N4 C8 O1 0.0
C7 N4 C8 O2 180.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126813
2 PubChem 139068780
