Recurrent Supramolecular Patterns in a Series of Salts of Heterocyclic Polyamines and Heterocyclic Dicarboxylic Acids: Synthesis, Single-Crystal X-ray Structure, Hirshfeld Surface Analysis, Energy Framework, and Quantum Chemical Calculations
Bojarska, Joanna; Łyczko, Krzysztof; Breza, Martin; Mieczkowski, Adam; Crystals 14 (2024) 733–; doi:10.3390/cryst14080733

data_1572515
_publ_section_title
;
 Recurrent Supramolecular Patterns in a Series of Salts of Heterocyclic
 Polyamines and Heterocyclic Dicarboxylic Acids: Synthesis, Single-Crystal
 X-ray Structure, Hirshfeld Surface Analysis, Energy Framework, and
 Quantum Chemical Calculations
;
_journal_issue                   8
_journal_name_full               Crystals
_journal_page_first              733
_journal_paper_doi               10.3390/cryst14080733
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C6 H3 O4 S, C4 H6 Cl N4'
_chemical_formula_sum            'C10 H9 Cl N4 O4 S'
_chemical_formula_weight         316.72
_chemical_name_systematic
'2,4-diamino-6-chloropyrimidin-3-ium 4-carboxythiophene-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-06-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.446(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2509(2)
_cell_length_b                   4.64879(11)
_cell_length_c                   27.0791(7)
_cell_measurement_reflns_used    8428
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      70.3350
_cell_measurement_theta_min      3.2460
_cell_volume                     1290.02(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0131
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -21.00  34.00   1.00    1.05    --    0.00 -77.00-180.00   55
  2  \w    -83.00 -37.00   1.00    1.05    --    0.00 178.00 150.00   46
  3  \w    -21.00  34.00   1.00    1.05    --    0.00 -77.00  60.00   55
  4  \w   -128.00 -76.00   1.00    4.50    --  -55.71-125.00  30.00   52
  5  \w   -129.00 -82.00   1.00    4.50    --  -55.71 -77.00 -90.00   47
  6  \w   -129.00 -82.00   1.00    4.50    --  -55.71 -77.00 -30.00   47
  7  \w   -128.00 -76.00   1.00    4.50    --  -55.71-125.00 -30.00   52
  8  \w   -129.00 -82.00   1.00    4.50    --  -55.71 -77.00  60.00   47
  9  \w    -86.00  -6.00   1.00    4.50    --  -55.71 125.00 -90.00   80
 10  \w   -131.00 -83.00   1.00    4.50    --  -55.71 -94.00  30.00   48
 11  \w   -128.00 -76.00   1.00    4.50    --  -55.71-125.00-150.00   52
 12  \w   -132.00 -15.00   1.00    4.50    --  -55.71 -30.00 120.00  117
 13  \w    -17.00  90.00   1.00    4.50    --   55.71 -77.00  30.00  107
 14  \w     29.00 125.00   1.00    4.50    --   55.71  61.00  30.00   96
 15  \w     29.00 125.00   1.00    4.50    --   55.71  61.00-180.00   96
 16  \w     84.00 178.00   1.00    5.50    --  111.41  50.00-180.00   94
 17  \w     37.00 106.00   1.00    5.50    --  111.41 -91.00  60.00   69
 18  \w     39.00 108.00   1.00    5.50    --  111.41-111.00-120.00   69
 19  \w     39.00 145.00   1.00    5.50    --  111.41 -76.00 -38.00  106
 20  \w     37.00 145.00   1.00    5.50    --  111.41 -37.00 -60.00  108
 21  \w     61.00 146.00   1.00    5.50    --  111.41 178.00  60.00   85
 22  \w    103.00 178.00   1.00    5.50    --  111.41  77.00 -60.00   75
 23  \w     84.00 178.00   1.00    5.50    --  111.41  50.00-120.00   94
 24  \w     78.00 178.00   1.00    5.50    --  111.41  37.00  60.00  100
 25  \w     84.00 178.00   1.00    5.50    --  111.41  63.00  90.00   94
 26  \w     84.00 178.00   1.00    5.50    --  111.41  50.00-150.00   94
 27  \w     78.00 178.00   1.00    5.50    --  111.41  37.00 150.00  100
 28  \w     38.00 146.00   1.00    5.50    --  111.41 -77.00 150.00  108
 29  \w    -21.00  34.00   1.00    1.05    --    0.00 -77.00-120.00   55
 30  \w    -83.00 -37.00   1.00    1.05    --    0.00 178.00   0.00   46
 31  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00  60.00   96
 32  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00-150.00   96
 33  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00-120.00   96
 34  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00 -60.00   96
 35  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00  90.00   96
 36  \w   -128.00 -76.00   1.00    4.50    --  -55.71-125.00 120.00   52
 37  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00   0.00   96
 38  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00 120.00   96
 39  \w    -86.00  -6.00   1.00    4.50    --  -55.71 125.00 150.00   80
 40  \w   -125.00 -29.00   1.00    4.50    --  -55.71 -61.00-180.00   96
 41  \w     27.00 112.00   1.00    4.50    --   55.71-125.00 -60.00   85
 42  \w     29.00 125.00   1.00    4.50    --   55.71  61.00  90.00   96
 43  \w     84.00 178.00   1.00    5.50    --  111.41  50.00   0.00   94
 44  \w     78.00 178.00   1.00    5.50    --  111.41  37.00 -30.00  100
 45  \w     84.00 178.00   1.00    5.50    --  111.41  63.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0587973000
_diffrn_orient_matrix_UB_12      0.2516115000
_diffrn_orient_matrix_UB_13      -0.0301619000
_diffrn_orient_matrix_UB_21      0.1381851000
_diffrn_orient_matrix_UB_22      0.1146469000
_diffrn_orient_matrix_UB_23      -0.0093278000
_diffrn_orient_matrix_UB_31      0.0057629000
_diffrn_orient_matrix_UB_32      -0.1827074000
_diffrn_orient_matrix_UB_33      -0.0473647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.065
_diffrn_reflns_theta_min         3.265
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.8126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2199
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k8a3
_cod_original_cell_volume        1290.03(5)
_cod_database_code               1572515
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C10 H9 Cl1 N4 O4 S1'
_chemical_oxdiff_usercomment     'colourless block, 100K, Cu, 0.18x0.05x0.043'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N4-H4A
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C1(H1)
;
_shelx_res_checksum              98448
_shelx_hkl_checksum              66578
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.730