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#$Date: 2023-01-21 10:48:55 +0200 (Sat, 21 Jan 2023) $
#$Revision: 280497 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106524.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106524
loop_
_publ_author_name
'Hussien, Nasry Jassim'
'Yusoff, Siti Fairus M.'
'El-Hiti, Gamal A.'
'Farina, Yang'
'Al-Jeboori, Mohamad J.'
'Yousif, Emad'
_publ_section_title
;
 Crystal structure of
 1-(4,4-dimethyl-2,6-dithioxo-1,3,5-triazinan-1-yl)-3-(diethylaminocarbonyl)thiourea,
 C11H20N6OS3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              325
_journal_page_last               326
_journal_paper_doi               10.1515/ncrs-2016-0265
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C11 H20 N6 O S3'
_chemical_formula_sum            'C11 H20 N6 O S3'
_chemical_formula_weight         348.51
_chemical_name_systematic
1-(4,4-Dimethyl-2,6-dithioxo-1,3,5-triazinan-1-yl)-3-(diethylaminocarbonyl)thiourea
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.658(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0196(17)
_cell_length_b                   13.416(2)
_cell_length_c                   13.267(2)
_cell_measurement_reflns_used    56717
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.04
_cell_volume                     1752.6(5)
_computing_cell_refinement       'SAINT [9]'
_computing_data_collection       'SMART [9]'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL-97 [10]'
_computing_publication_material  'SHELXTL and PLATON [11]'
_computing_structure_refinement  'SHELXL-97 [10]'
_computing_structure_solution    'SHELXS-97 [10]'
_diffrn_ambient_temperature      303(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scan'
_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  0.1187
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49159
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_correction_T_min  0.7823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2009)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0558
_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)+(0.0526P)²+2.0786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2162
_reflns_number_total             3452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0265_suppl.cif
_cod_data_source_block           yf50_0m
_cod_original_cell_volume        1752.7(5)
_cod_original_sg_symbol_H-M      p21/c
_cod_database_code               8106524
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09032(11) 0.12038(8) 0.59108(9) 0.0640(3) Uani 1 1 d . . .
S2 S 0.35778(11) 0.06218(8) 0.39340(7) 0.0529(3) Uani 1 1 d . . .
S3 S 0.44664(13) 0.10000(8) 0.79953(7) 0.0647(4) Uani 1 1 d . . .
O1 O 0.3125(3) -0.17590(18) 0.64806(19) 0.0494(6) Uani 1 1 d . . .
N1 N 0.1076(3) -0.2347(2) 0.6740(3) 0.0547(9) Uani 1 1 d . . .
N2 N 0.1288(3) -0.0707(2) 0.6277(3) 0.0544(9) Uani 1 1 d D . .
N3 N 0.3178(3) 0.0167(2) 0.6034(2) 0.0426(7) Uani 1 1 d D . .
N4 N 0.3827(3) 0.10545(19) 0.59415(19) 0.0387(7) Uani 1 1 d . . .
N5 N 0.4713(3) 0.2186(2) 0.4953(2) 0.0426(7) Uani 1 1 d D . .
N6 N 0.5076(3) 0.2364(2) 0.6735(2) 0.0443(8) Uani 1 1 d D . .
C1 C -0.0329(6) -0.1572(4) 0.7885(5) 0.1051(19) Uani 1 1 d . . .
H1A H 0.0181 -0.1927 0.8457 0.158 Uiso 1 1 calc R . .
H1B H -0.1251 -0.1497 0.7979 0.158 Uiso 1 1 calc R . .
H1C H 0.0067 -0.0926 0.7837 0.158 Uiso 1 1 calc R . .
C2 C -0.0305(4) -0.2149(3) 0.6909(4) 0.0695(13) Uani 1 1 d . . .
H2A H -0.0773 -0.2779 0.6939 0.083 Uiso 1 1 calc R . .
H2B H -0.0794 -0.1775 0.6331 0.083 Uiso 1 1 calc R . .
C3 C 0.1565(5) -0.3372(3) 0.6890(4) 0.0714(13) Uani 1 1 d . . .
H3A H 0.1323 -0.3637 0.7512 0.086 Uiso 1 1 calc R . .
H3B H 0.2547 -0.3377 0.6973 0.086 Uiso 1 1 calc R . .
C4 C 0.0971(7) -0.4030(4) 0.5997(5) 0.119(2) Uani 1 1 d . . .
H4A H 0.0005 -0.4073 0.5949 0.178 Uiso 1 1 calc R . .
H4B H 0.1361 -0.4685 0.6100 0.178 Uiso 1 1 calc R . .
H4C H 0.1170 -0.3752 0.5375 0.178 Uiso 1 1 calc R . .
C5 C 0.1911(4) -0.1634(3) 0.6497(3) 0.0455(9) Uani 1 1 d . . .
C6 C 0.1863(4) 0.0188(3) 0.6077(3) 0.0459(9) Uani 1 1 d . . .
C7 C 0.4065(3) 0.1329(2) 0.4963(2) 0.0376(8) Uani 1 1 d . . .
C8 C 0.4898(4) 0.2929(2) 0.5775(2) 0.0409(8) Uani 1 1 d . . .
C9 C 0.6180(4) 0.3513(3) 0.5755(3) 0.0577(11) Uani 1 1 d . . .
H9A H 0.6932 0.3062 0.5796 0.087 Uiso 1 1 calc R . .
H9B H 0.6344 0.3962 0.6328 0.087 Uiso 1 1 calc R . .
H9C H 0.6080 0.3887 0.5129 0.087 Uiso 1 1 calc R . .
C10 C 0.3635(5) 0.3587(3) 0.5676(3) 0.0642(12) Uani 1 1 d . . .
H10A H 0.3516 0.3948 0.5041 0.096 Uiso 1 1 calc R . .
H10B H 0.3743 0.4049 0.6237 0.096 Uiso 1 1 calc R . .
H10C H 0.2853 0.3177 0.5687 0.096 Uiso 1 1 calc R . .
C11 C 0.4464(4) 0.1516(2) 0.6858(2) 0.0407(8) Uani 1 1 d . . .
H2 H 0.0408(12) -0.065(3) 0.620(4) 0.086(16) Uiso 1 1 d D . .
H3 H 0.366(3) -0.0375(17) 0.614(3) 0.061(12) Uiso 1 1 d D . .
H5 H 0.487(4) 0.239(3) 0.4371(16) 0.072(14) Uiso 1 1 d D . .
H6 H 0.550(3) 0.265(3) 0.7288(18) 0.065(13) Uiso 1 1 d D . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N1 C3 119.5(3) . .
C5 N1 C2 123.6(3) . .
C3 N1 C2 116.8(3) . .
C6 N2 C5 129.0(3) . .
C6 N2 H2 111(3) . .
C5 N2 H2 120(3) . .
C6 N3 N4 118.4(3) . .
C6 N3 H3 123(3) . .
N4 N3 H3 119(3) . .
N3 N4 C11 116.8(3) . .
N3 N4 C7 118.2(3) . .
C11 N4 C7 123.6(3) . .
C7 N5 C8 125.4(3) . .
C7 N5 H5 117(3) . .
C8 N5 H5 116(3) . .
C11 N6 C8 124.8(3) . .
C11 N6 H6 117(3) . .
C8 N6 H6 118(3) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C1 112.8(4) . .
N1 C2 H2A 109.0 . .
C1 C2 H2A 109.0 . .
N1 C2 H2B 109.0 . .
C1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
N1 C3 C4 111.8(4) . .
N1 C3 H3A 109.3 . .
C4 C3 H3A 109.3 . .
N1 C3 H3B 109.3 . .
C4 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C5 N1 124.5(3) . .
O1 C5 N2 121.4(3) . .
N1 C5 N2 114.1(3) . .
N3 C6 N2 116.3(3) . .
N3 C6 S1 124.5(3) . .
N2 C6 S1 119.2(3) . .
N5 C7 N4 113.8(3) . .
N5 C7 S2 124.0(3) . .
N4 C7 S2 122.2(3) . .
N5 C8 N6 105.9(3) . .
N5 C8 C9 109.3(3) . .
N6 C8 C9 108.5(3) . .
N5 C8 C10 109.9(3) . .
N6 C8 C10 109.9(3) . .
C9 C8 C10 113.1(3) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N6 C11 N4 114.8(3) . .
N6 C11 S3 123.4(3) . .
N4 C11 S3 121.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C6 1.659(4) .
S2 C7 1.660(3) .
S3 C11 1.660(3) .
O1 C5 1.232(4) .
N1 C5 1.348(4) .
N1 C3 1.462(5) .
N1 C2 1.466(5) .
N2 C6 1.378(5) .
N2 C5 1.398(5) .
N2 H2 0.872(10) .
N3 C6 1.329(5) .
N3 N4 1.373(4) .
N3 H3 0.872(10) .
N4 C11 1.408(4) .
N4 C7 1.412(4) .
N5 C7 1.322(4) .
N5 C8 1.463(4) .
N5 H5 0.860(10) .
N6 C11 1.317(4) .
N6 C8 1.464(4) .
N6 H6 0.868(10) .
C1 C2 1.513(7) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.508(7) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C8 C9 1.509(5) .
C8 C10 1.529(5) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N3 N4 C11 92.4(4) . . . .
C6 N3 N4 C7 -100.9(4) . . . .
C5 N1 C2 C1 -69.9(5) . . . .
C3 N1 C2 C1 107.6(5) . . . .
C5 N1 C3 C4 -105.5(5) . . . .
C2 N1 C3 C4 76.9(5) . . . .
C3 N1 C5 O1 -7.1(6) . . . .
C2 N1 C5 O1 170.3(4) . . . .
C3 N1 C5 N2 174.1(4) . . . .
C2 N1 C5 N2 -8.5(5) . . . .
C6 N2 C5 O1 -4.1(6) . . . .
C6 N2 C5 N1 174.7(4) . . . .
N4 N3 C6 N2 -173.5(3) . . . .
N4 N3 C6 S1 6.4(5) . . . .
C5 N2 C6 N3 3.8(6) . . . .
C5 N2 C6 S1 -176.0(3) . . . .
C8 N5 C7 N4 -14.6(5) . . . .
C8 N5 C7 S2 166.0(3) . . . .
N3 N4 C7 N5 -179.0(3) . . . .
C11 N4 C7 N5 -13.3(5) . . . .
N3 N4 C7 S2 0.4(4) . . . .
C11 N4 C7 S2 166.1(3) . . . .
C7 N5 C8 N6 35.7(5) . . . .
C7 N5 C8 C9 152.4(3) . . . .
C7 N5 C8 C10 -82.9(4) . . . .
C11 N6 C8 N5 -34.7(5) . . . .
C11 N6 C8 C9 -152.0(3) . . . .
C11 N6 C8 C10 84.0(4) . . . .
C8 N6 C11 N4 13.2(5) . . . .
C8 N6 C11 S3 -168.6(3) . . . .
N3 N4 C11 N6 179.9(3) . . . .
C7 N4 C11 N6 14.0(5) . . . .
N3 N4 C11 S3 1.6(4) . . . .
C7 N4 C11 S3 -164.3(3) . . . .
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{11568081-20de-4e5f-af23-e555c0954d63} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{11568081-20de-4e5f-af23-e555c0954d63} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
