#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/76/7227680.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_7227680
loop_
_publ_author_name
'Saeed, Aamer'
'Flörke, Ulrich'
'Fantoni, Adolfo'
'Khurshid, Asma'
'Pérez, Hiram'
'Erben, Mauricio F.'
_publ_section_title
;
 Close insight into the nature of intermolecular interactions in
 dihydropyrimidine-2(1H)-thione derivatives
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1495
_journal_paper_doi               10.1039/C6CE02619B
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C14 H18 N2 O S'
_chemical_formula_weight         262.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-13 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                64.578(5)
_cell_angle_beta                 78.685(6)
_cell_angle_gamma                63.892(6)
_cell_formula_units_Z            2
_cell_length_a                   8.729(3)
_cell_length_b                   9.683(3)
_cell_length_c                   10.503(4)
_cell_measurement_reflns_used    762
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.54
_cell_volume                     719.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.1211
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5079
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0522
_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)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1687
_reflns_number_total             3133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce02619b2.cif
_cod_data_source_block           s2365
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7227677--7227680.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7227680
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
S1 S 0.24012(9) 0.81042(8) 0.11180(7) 0.0379(2) Uani 1 1 d .
O1 O 0.8395(2) 0.1345(2) 0.39205(17) 0.0428(5) Uani 1 1 d .
N1 N 0.1569(3) 0.5485(3) 0.2528(2) 0.0394(6) Uani 1 1 d .
N2 N -0.0568(2) 0.7944(2) 0.1238(2) 0.0383(6) Uani 1 1 d .
H2 H -0.0894 0.9023 0.0738 0.046 Uiso 1 1 calc R
C1 C 0.3364(3) 0.4476(3) 0.2842(3) 0.0368(6) Uani 1 1 d .
C2 C 0.4418(4) 0.3823(3) 0.1912(3) 0.0441(7) Uani 1 1 d .
H2A H 0.3976 0.4096 0.1037 0.053 Uiso 1 1 calc R
C3 C 0.6119(3) 0.2770(3) 0.2220(3) 0.0422(7) Uani 1 1 d .
H3A H 0.6840 0.2317 0.1568 0.051 Uiso 1 1 calc R
C4 C 0.6747(3) 0.2389(3) 0.3494(3) 0.0359(6) Uani 1 1 d .
C5 C 0.5693(3) 0.3073(3) 0.4429(3) 0.0390(7) Uani 1 1 d .
H5A H 0.6131 0.2817 0.5299 0.047 Uiso 1 1 calc R
C6 C 0.4003(3) 0.4127(3) 0.4098(3) 0.0386(7) Uani 1 1 d .
H6A H 0.3283 0.4609 0.4733 0.046 Uiso 1 1 calc R
C7 C 0.9531(3) 0.0645(3) 0.2977(3) 0.0525(8) Uani 1 1 d .
H7A H 0.9100 -0.0024 0.2784 0.079 Uiso 1 1 calc R
H7B H 1.0662 -0.0066 0.3403 0.079 Uiso 1 1 calc R
H7C H 0.9613 0.1545 0.2093 0.079 Uiso 1 1 calc R
C8 C 0.0380(4) 0.4701(3) 0.3058(3) 0.0448(7) Uani 1 1 d .
C9 C -0.1222(3) 0.5561(3) 0.2600(3) 0.0500(8) Uani 1 1 d .
H9A H -0.1994 0.5031 0.3003 0.060 Uiso 1 1 calc R
C10 C -0.1891(3) 0.7282(3) 0.1508(3) 0.0398(7) Uani 1 1 d .
C11 C 0.1039(3) 0.7127(3) 0.1650(2) 0.0340(6) Uani 1 1 d .
C12 C 0.1023(4) 0.2961(4) 0.4119(3) 0.0767(11) Uani 1 1 d .
H12A H 0.0126 0.2539 0.4351 0.115 Uiso 1 1 calc R
H12B H 0.1347 0.2936 0.4973 0.115 Uiso 1 1 calc R
H12C H 0.2020 0.2258 0.3735 0.115 Uiso 1 1 calc R
C13 C -0.2251(4) 0.7285(4) 0.0142(3) 0.0632(9) Uani 1 1 d .
H13A H -0.2614 0.8423 -0.0583 0.095 Uiso 1 1 calc R
H13B H -0.3158 0.6888 0.0307 0.095 Uiso 1 1 calc R
H13C H -0.1213 0.6547 -0.0177 0.095 Uiso 1 1 calc R
C14 C -0.3518(3) 0.8431(3) 0.1992(3) 0.0512(8) Uani 1 1 d .
H14A H -0.3295 0.8450 0.2863 0.077 Uiso 1 1 calc R
H14B H -0.4414 0.8019 0.2168 0.077 Uiso 1 1 calc R
H14C H -0.3890 0.9563 0.1259 0.077 Uiso 1 1 calc R
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
C4 O1 C7 117.7(2)
C11 N1 C8 120.5(2)
C11 N1 C1 120.1(2)
C8 N1 C1 119.2(2)
C11 N2 C10 128.5(2)
C2 C1 C6 119.9(2)
C2 C1 N1 119.8(2)
C6 C1 N1 120.2(2)
C1 C2 C3 121.2(2)
C4 C3 C2 118.8(3)
O1 C4 C3 123.9(2)
O1 C4 C5 115.9(2)
C3 C4 C5 120.2(2)
C6 C5 C4 120.1(2)
C1 C6 C5 119.8(2)
C9 C8 N1 119.3(2)
C9 C8 C12 123.6(3)
N1 C8 C12 117.0(2)
C8 C9 C10 125.0(3)
N2 C10 C9 107.4(2)
N2 C10 C14 108.2(2)
C9 C10 C14 112.1(2)
N2 C10 C13 109.2(2)
C9 C10 C13 111.0(2)
C14 C10 C13 108.9(2)
N2 C11 N1 118.1(2)
N2 C11 S1 121.0(2)
N1 C11 S1 120.86(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.702(3)
O1 C4 1.369(3)
O1 C7 1.423(3)
N1 C11 1.362(3)
N1 C8 1.438(3)
N1 C1 1.448(3)
N2 C11 1.322(3)
N2 C10 1.481(3)
C1 C2 1.366(3)
C1 C6 1.380(3)
C2 C3 1.386(3)
C3 C4 1.384(3)
C4 C5 1.384(3)
C5 C6 1.382(3)
C8 C9 1.333(3)
C8 C12 1.482(3)
C9 C10 1.483(3)
C10 C14 1.525(3)
C10 C13 1.527(4)
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
C11 N1 C1 C2 -81.3(3)
C8 N1 C1 C2 93.6(3)
C11 N1 C1 C6 100.9(3)
C8 N1 C1 C6 -84.3(3)
C6 C1 C2 C3 1.8(4)
N1 C1 C2 C3 -176.0(2)
C1 C2 C3 C4 -0.3(4)
C7 O1 C4 C3 1.6(4)
C7 O1 C4 C5 -178.6(2)
C2 C3 C4 O1 178.9(2)
C2 C3 C4 C5 -0.9(4)
O1 C4 C5 C6 -179.2(2)
C3 C4 C5 C6 0.6(4)
C2 C1 C6 C5 -2.1(4)
N1 C1 C6 C5 175.7(2)
C4 C5 C6 C1 0.9(4)
C11 N1 C8 C9 5.0(4)
C1 N1 C8 C9 -169.8(3)
C11 N1 C8 C12 -174.0(2)
C1 N1 C8 C12 11.2(4)
N1 C8 C9 C10 3.1(4)
C12 C8 C9 C10 -178.0(3)
C11 N2 C10 C9 11.9(4)
C11 N2 C10 C14 133.1(3)
C11 N2 C10 C13 -108.5(3)
C8 C9 C10 N2 -10.2(4)
C8 C9 C10 C14 -129.0(3)
C8 C9 C10 C13 109.0(3)
C10 N2 C11 N1 -5.6(4)
C10 N2 C11 S1 175.27(19)
C8 N1 C11 N2 -3.9(3)
C1 N1 C11 N2 170.9(2)
C8 N1 C11 S1 175.28(19)
C1 N1 C11 S1 -9.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 776856
