#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/81/7218129.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_7218129
loop_
_publ_author_name
'Ostasz, A.'
'Łyszczek, R.'
'Mazur, L.'
'Tarasiuk, B.'
_publ_section_title
;
 Co-crystal formation between 2-amino-4,6-dimethylpyrimidine and new
 p-xylylene-bis(thioacetic) acid
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              10262
_journal_paper_doi               10.1039/C4CE01567C
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H14 O4 S2, 2(C6 H9 N3)'
_chemical_formula_sum            'C24 H32 N6 O4 S2'
_chemical_formula_weight         532.68
_chemical_melting_point          425.15
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.069(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.6366(18)
_cell_length_b                   4.8355(5)
_cell_length_c                   15.5930(17)
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9491
_cell_measurement_theta_min      2.5419
_cell_volume                     1322.3(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_molecular_graphics
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.4221
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8987
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1077P)²+0.0552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1565
_reflns_number_gt                2354
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01567c2.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '152\%C' was changed to '425.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7218128--7218131.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218129
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
C1 C 0.24551(11) 0.2524(4) 0.58623(13) 0.0245(4) Uani 1 1 d .
C2 C 0.29917(12) 0.0223(4) 0.61995(13) 0.0258(4) Uani 1 1 d .
H2A H 0.3214 -0.0624 0.5720 0.031 Uiso 1 1 calc R
H2B H 0.2705 -0.1186 0.6469 0.031 Uiso 1 1 calc R
C3 C 0.43417(13) 0.3416(4) 0.62824(14) 0.0287(5) Uani 1 1 d .
H3A H 0.4033 0.4852 0.5984 0.034 Uiso 1 1 calc R
H3B H 0.4753 0.4315 0.6641 0.034 Uiso 1 1 calc R
C4 C 0.46807(11) 0.1652(4) 0.56219(14) 0.0248(4) Uani 1 1 d .
C5 C 0.44170(12) 0.1845(4) 0.47388(14) 0.0278(5) Uani 1 1 d .
H5 H 0.4026 0.3070 0.4559 0.033 Uiso 1 1 calc R
C6 C 0.47357(11) 0.0223(5) 0.41333(14) 0.0277(5) Uani 1 1 d .
H6 H 0.4556 0.0393 0.3553 0.033 Uiso 1 1 calc R
C7 C 0.11302(11) 0.8566(4) 0.46685(13) 0.0241(4) Uani 1 1 d .
C8 C 0.10001(12) 1.1608(4) 0.35263(14) 0.0263(4) Uani 1 1 d .
C9 C 0.16951(12) 1.0696(4) 0.32630(14) 0.0273(5) Uani 1 1 d .
H9 H 0.1879 1.1412 0.2771 0.033 Uiso 1 1 calc R
C10 C 0.20970(12) 0.8706(4) 0.37563(13) 0.0243(4) Uani 1 1 d .
C11 C 0.05479(15) 1.3821(5) 0.30311(17) 0.0332(5) Uani 1 1 d .
C12 C 0.28467(13) 0.7573(5) 0.35426(16) 0.0298(5) Uani 1 1 d .
O1 O 0.26570(8) 0.3702(3) 0.51653(10) 0.0276(4) Uani 1 1 d .
O2 O 0.18982(9) 0.3183(4) 0.62231(10) 0.0353(4) Uani 1 1 d .
N1 N 0.18157(9) 0.7625(4) 0.44631(11) 0.0230(4) Uani 1 1 d .
N2 N 0.08425(10) 0.7427(4) 0.53451(12) 0.0299(4) Uani 1 1 d .
N3 N 0.07162(10) 1.0558(4) 0.42184(11) 0.0264(4) Uani 1 1 d .
S1 S 0.37518(3) 0.15026(11) 0.69804(3) 0.02698(19) Uani 1 1 d .
H21 H 0.1085 0.6123 0.5616 0.040 Uiso 1 1 d .
H1O H 0.2370 0.5181 0.4991 0.040 Uiso 1 1 d .
H22 H 0.0475 0.8048 0.5531 0.040 Uiso 1 1 d .
H11A H 0.001(2) 1.358(6) 0.306(2) 0.060(10) Uiso 1 1 d .
H11B H 0.0636(19) 1.556(8) 0.323(2) 0.060(9) Uiso 1 1 d .
H11C H 0.061(2) 1.377(7) 0.237(2) 0.071(11) Uiso 1 1 d .
H12A H 0.3197(18) 0.770(7) 0.404(2) 0.049(8) Uiso 1 1 d .
H12B H 0.2803(16) 0.569(6) 0.3403(17) 0.039(7) Uiso 1 1 d .
H12C H 0.3014(16) 0.851(5) 0.3008(18) 0.037(7) 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'
O O 0.0106 0.0060 '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'
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
O2 C1 O1 124.73(19) . .
O2 C1 C2 122.18(19) . .
O1 C1 C2 113.08(17) . .
C1 C2 S1 111.73(15) . .
C1 C2 H2A 109.3 . .
S1 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
S1 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
C4 C3 S1 114.23(15) . .
C4 C3 H3A 108.7 . .
S1 C3 H3A 108.7 . .
C4 C3 H3B 108.7 . .
S1 C3 H3B 108.7 . .
H3A C3 H3B 107.6 . .
C6 C4 C5 117.93(19) 3_656 .
C6 C4 C3 121.01(19) 3_656 .
C5 C4 C3 121.05(19) . .
C6 C5 C4 120.70(19) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C4 121.36(19) . 3_656
C5 C6 H6 119.3 . .
C4 C6 H6 119.3 3_656 .
N2 C7 N3 118.14(18) . .
N2 C7 N1 117.96(18) . .
N3 C7 N1 123.89(19) . .
N3 C8 C9 122.01(19) . .
N3 C8 C11 117.5(2) . .
C9 C8 C11 120.4(2) . .
C10 C9 C8 117.9(2) . .
C10 C9 H9 121.0 . .
C8 C9 H9 121.0 . .
N1 C10 C9 120.64(19) . .
N1 C10 C12 116.43(18) . .
C9 C10 C12 122.9(2) . .
C8 C11 H11A 111.4(19) . .
C8 C11 H11B 115(2) . .
H11A C11 H11B 103(3) . .
C8 C11 H11C 112(2) . .
H11A C11 H11C 105(3) . .
H11B C11 H11C 109(3) . .
C10 C12 H12A 108.3(19) . .
C10 C12 H12B 110.7(18) . .
H12A C12 H12B 106(3) . .
C10 C12 H12C 111.0(16) . .
H12A C12 H12C 115(3) . .
H12B C12 H12C 105(2) . .
C1 O1 H1O 113.7 . .
C10 N1 C7 118.14(17) . .
C7 N2 H21 119.0 . .
C7 N2 H22 121.6 . .
H21 N2 H22 119.1 . .
C8 N3 C7 117.35(18) . .
C2 S1 C3 101.44(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.225(3) .
C1 O1 1.310(3) .
C1 C2 1.518(3) .
C2 S1 1.821(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.509(3) .
C3 S1 1.834(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C6 1.394(3) 3_656
C4 C5 1.409(3) .
C5 C6 1.391(3) .
C5 H5 0.9300 .
C6 C4 1.394(3) 3_656
C6 H6 0.9300 .
C7 N2 1.337(3) .
C7 N3 1.359(3) .
C7 N1 1.361(3) .
C8 N3 1.337(3) .
C8 C9 1.404(3) .
C8 C11 1.499(3) .
C9 C10 1.380(3) .
C9 H9 0.9300 .
C10 N1 1.360(3) .
C10 C12 1.501(3) .
C11 H11A 0.96(4) .
C11 H11B 0.91(4) .
C11 H11C 1.05(4) .
C12 H12A 0.94(3) .
C12 H12B 0.94(3) .
C12 H12C 1.02(3) .
O1 H1O 0.9013 .
N2 H21 0.8489 .
N2 H22 0.7962 .
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_4
O2 C1 C2 S1 -88.3(2) . .
O1 C1 C2 S1 91.09(19) . .
S1 C3 C4 C6 -71.1(2) . 3_656
S1 C3 C4 C5 108.8(2) . .
C6 C4 C5 C6 -0.5(3) 3_656 .
C3 C4 C5 C6 179.60(19) . .
C4 C5 C6 C4 0.5(3) . 3_656
N3 C8 C9 C10 -1.7(3) . .
C11 C8 C9 C10 178.3(2) . .
C8 C9 C10 N1 1.5(3) . .
C8 C9 C10 C12 -179.8(2) . .
C9 C10 N1 C7 -0.1(3) . .
C12 C10 N1 C7 -178.84(19) . .
N2 C7 N1 C10 177.60(18) . .
N3 C7 N1 C10 -1.3(3) . .
C9 C8 N3 C7 0.4(3) . .
C11 C8 N3 C7 -179.58(19) . .
N2 C7 N3 C8 -177.77(19) . .
N1 C7 N3 C8 1.1(3) . .
C1 C2 S1 C3 -72.30(16) . .
C4 C3 S1 C2 -62.47(18) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199191
