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#$Date: 2023-03-23 10:37:37 +0200 (Thu, 23 Mar 2023) $
#$Revision: 281997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106946.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_8106946
loop_
_publ_author_name
'Al-Tamimi, Abdul-Malek S.'
'Ghabbour, Hazem A.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 6-oxo-4-propyl-2-(propylthio)-1,6-dihydropyrimidine-5-carbonitrile,
 C11H15N3OS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              583
_journal_page_last               585
_journal_paper_doi               10.1515/ncrs-2015-0198
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C11 H15 N3 O S'
_chemical_formula_weight         237.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                87.982(2)
_cell_angle_beta                 87.330(2)
_cell_angle_gamma                78.403(2)
_cell_formula_units_Z            2
_cell_length_a                   4.6579(2)
_cell_length_b                   9.6316(5)
_cell_length_c                   13.6654(7)
_cell_measurement_reflns_used    9432
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.59
_cell_volume                     599.69(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0770
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30731
_diffrn_reflns_theta_full        33.19
_diffrn_reflns_theta_max         33.19
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.8886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         4565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0450
_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)+(0.0770P)²+0.1258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                3906
_reflns_number_total             4565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0198_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106946
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.92108(6) 0.29522(3) 0.054065(19) 0.01591(9) Uani 1 1 d . . .
O1 O 0.34147(18) -0.07114(8) 0.10536(6) 0.01943(17) Uani 1 1 d . . .
N1 N 0.72600(19) 0.21810(9) 0.23138(7) 0.01427(17) Uani 1 1 d . . .
N2 N 0.62070(19) 0.09815(9) 0.09428(7) 0.01440(17) Uani 1 1 d . . .
N3 N 0.1192(2) -0.10210(11) 0.35935(8) 0.0235(2) Uani 1 1 d . . .
C1 C 0.4574(2) 0.01415(10) 0.14710(8) 0.01416(18) Uani 1 1 d . . .
C2 C 0.4343(2) 0.03894(10) 0.25060(7) 0.01348(18) Uani 1 1 d . . .
C3 C 0.5703(2) 0.13838(10) 0.28932(8) 0.01356(18) Uani 1 1 d . . .
C4 C 0.7417(2) 0.19636(10) 0.13722(8) 0.01312(18) Uani 1 1 d . . .
C5 C 0.2623(2) -0.04047(11) 0.31073(8) 0.01612(19) Uani 1 1 d . . .
C6 C 0.5458(2) 0.17129(11) 0.39577(8) 0.01672(19) Uani 1 1 d . . .
H6A H 0.7445 0.1658 0.4203 0.020 Uiso 1 1 calc R . .
H6B H 0.4557 0.0995 0.4326 0.020 Uiso 1 1 calc R . .
C7 C 0.3607(3) 0.31897(12) 0.41438(8) 0.0205(2) Uani 1 1 d . . .
H7A H 0.4528 0.3912 0.3789 0.025 Uiso 1 1 calc R . .
H7B H 0.1628 0.3253 0.3889 0.025 Uiso 1 1 calc R . .
C8 C 0.3334(3) 0.34930(13) 0.52337(9) 0.0258(2) Uani 1 1 d . . .
H8A H 0.2219 0.4458 0.5332 0.039 Uiso 1 1 calc R . .
H8B H 0.5294 0.3402 0.5491 0.039 Uiso 1 1 calc R . .
H8C H 0.2312 0.2814 0.5580 0.039 Uiso 1 1 calc R . .
C9 C 1.0327(2) 0.42019(11) 0.13338(8) 0.01578(19) Uani 1 1 d . . .
H9A H 1.1096 0.3689 0.1937 0.019 Uiso 1 1 calc R . .
H9B H 1.1949 0.4579 0.0998 0.019 Uiso 1 1 calc R . .
C10 C 0.7891(2) 0.54439(11) 0.16233(9) 0.0185(2) Uani 1 1 d . . .
H10A H 0.6368 0.5092 0.2034 0.022 Uiso 1 1 calc R . .
H10B H 0.6965 0.5909 0.1027 0.022 Uiso 1 1 calc R . .
C11 C 0.9111(3) 0.65190(13) 0.21904(9) 0.0248(2) Uani 1 1 d . . .
H11A H 0.7499 0.7280 0.2405 0.037 Uiso 1 1 calc R . .
H11B H 1.0509 0.6921 0.1766 0.037 Uiso 1 1 calc R . .
H11C H 1.0108 0.6047 0.2764 0.037 Uiso 1 1 calc R . .
H1N2 H 0.632(4) 0.090(2) 0.0289(15) 0.040(5) Uiso 1 1 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
C4 S1 C9 101.90(5) . .
C4 N1 C3 117.18(9) . .
C4 N2 C1 122.27(9) . .
C4 N2 H1N2 120.5(12) . .
C1 N2 H1N2 117.1(12) . .
O1 C1 N2 120.75(10) . .
O1 C1 C2 125.42(10) . .
N2 C1 C2 113.81(9) . .
C3 C2 C5 121.73(9) . .
C3 C2 C1 120.55(9) . .
C5 C2 C1 117.70(9) . .
N1 C3 C2 121.78(9) . .
N1 C3 C6 115.47(9) . .
C2 C3 C6 122.68(9) . .
N1 C4 N2 124.35(9) . .
N1 C4 S1 122.12(8) . .
N2 C4 S1 113.53(8) . .
N3 C5 C2 178.61(11) . .
C3 C6 C7 111.75(9) . .
C3 C6 H6A 109.3 . .
C7 C6 H6A 109.3 . .
C3 C6 H6B 109.3 . .
C7 C6 H6B 109.3 . .
H6A C6 H6B 107.9 . .
C8 C7 C6 110.94(9) . .
C8 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.0 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 S1 114.46(7) . .
C10 C9 H9A 108.6 . .
S1 C9 H9A 108.6 . .
C10 C9 H9B 108.6 . .
S1 C9 H9B 108.6 . .
H9A C9 H9B 107.6 . .
C9 C10 C11 110.59(9) . .
C9 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.7469(10) .
S1 C9 1.8137(11) .
O1 C1 1.2376(12) .
N1 C4 1.3072(13) .
N1 C3 1.3675(13) .
N2 C4 1.3568(13) .
N2 C1 1.3819(13) .
N2 H1N2 0.90(2) .
N3 C5 1.1526(15) .
C1 C2 1.4381(14) .
C2 C3 1.3817(14) .
C2 C5 1.4292(14) .
C3 C6 1.4940(14) .
C6 C7 1.5309(15) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.5223(16) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.5234(15) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.5264(16) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
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
C4 N2 C1 O1 177.52(10) . . . .
C4 N2 C1 C2 -1.21(14) . . . .
O1 C1 C2 C3 -179.17(10) . . . .
N2 C1 C2 C3 -0.51(14) . . . .
O1 C1 C2 C5 -0.38(16) . . . .
N2 C1 C2 C5 178.28(8) . . . .
C4 N1 C3 C2 -0.06(14) . . . .
C4 N1 C3 C6 -177.22(9) . . . .
C5 C2 C3 N1 -177.57(9) . . . .
C1 C2 C3 N1 1.17(15) . . . .
C5 C2 C3 C6 -0.62(15) . . . .
C1 C2 C3 C6 178.12(9) . . . .
C3 N1 C4 N2 -1.77(15) . . . .
C3 N1 C4 S1 177.48(7) . . . .
C1 N2 C4 N1 2.50(16) . . . .
C1 N2 C4 S1 -176.81(7) . . . .
C9 S1 C4 N1 -2.76(10) . . . .
C9 S1 C4 N2 176.56(7) . . . .
C3 C2 C5 N3 74(5) . . . .
C1 C2 C5 N3 -104(5) . . . .
N1 C3 C6 C7 67.19(12) . . . .
C2 C3 C6 C7 -109.94(11) . . . .
C3 C6 C7 C8 178.88(10) . . . .
C4 S1 C9 C10 -78.78(8) . . . .
S1 C9 C10 C11 -173.55(8) . . . .
