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_1572514
_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 H7 N4'
_chemical_formula_sum            'C10 H10 N4 O4 S'
_chemical_formula_weight         282.28
_chemical_name_systematic
'2,4-diaminopyrimidin-1-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                 96.586(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9538(3)
_cell_length_b                   3.79977(11)
_cell_length_c                   27.1930(7)
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      69.7040
_cell_measurement_theta_min      4.5800
_cell_volume                     1124.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_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 0.991
_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    -86.00 -39.00   1.00    1.00    --    0.00-178.00  30.00   47
  2  \w    -86.00 -39.00   1.00    1.00    --    0.00-178.00-150.00   47
  3  \w    -21.00  37.00   1.00    1.00    --    0.00 -77.00-120.00   58
  4  \w   -130.00 -76.00   1.00    1.00    --  -53.50-125.00  60.00   54
  5  \w   -133.00 -83.00   1.00    1.00    --  -53.50 -94.00-180.00   50
  6  \w   -129.00 -19.00   1.00    1.00    --  -53.50 -45.00  90.00  110
  7  \w   -129.00 -82.00   1.00    1.00    --  -53.50 -77.00 -90.00   47
  8  \w    -87.00  -6.00   1.00    1.00    --  -53.50 125.00 -60.00   81
  9  \w    -87.00  -6.00   1.00    1.00    --  -53.50 125.00-180.00   81
 10  \w   -130.00 -76.00   1.00    1.00    --  -53.50-125.00 150.00   54
 11  \w      1.00 102.00   1.00    1.00    --   56.00 -94.00  60.00  101
 12  \w     26.00 128.00   1.00    1.00    --   56.00  61.00   0.00  102
 13  \w     90.00 175.00   1.00    1.00    --  112.00 138.00 150.00   85
 14  \w     90.00 175.00   1.00    1.00    --  112.00 138.00-180.00   85
 15  \w     33.00 107.00   1.00    1.00    --  112.00 -91.00-180.00   74
 16  \w     35.00 153.00   1.00    1.00    --  112.00 -37.00  30.00  118
 17  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   75
 18  \w     38.00 143.00   1.00    1.00    --  112.00 -50.00-180.00  105
 19  \w     32.00 108.00   1.00    1.00    --  112.00-104.00 -90.00   76
 20  \w     32.00 108.00   1.00    1.00    --  112.00-104.00  90.00   76
 21  \w     81.00 178.00   1.00    1.00    --  112.00  50.00  30.00   97
 22  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 120.00   75
 23  \w     32.00 108.00   1.00    1.00    --  112.00-104.00 150.00   76
 24  \w     35.00 178.00   1.00    1.00    --  112.00  12.00 -60.00  143
 25  \w     37.00 149.00   1.00    1.00    --  112.00 -77.00-120.00  112
;
_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      0.0458143000
_diffrn_orient_matrix_UB_12      0.1007739000
_diffrn_orient_matrix_UB_13      0.0538344000
_diffrn_orient_matrix_UB_21      0.0625862000
_diffrn_orient_matrix_UB_22      -0.3619237000
_diffrn_orient_matrix_UB_23      0.0078256000
_diffrn_orient_matrix_UB_31      0.1184748000
_diffrn_orient_matrix_UB_32      0.1522835000
_diffrn_orient_matrix_UB_33      -0.0171091000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7405
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.787
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.668
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0556P)^2^+0.6356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1913
_reflns_number_total             2123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k8a2
_cod_database_code               1572514
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C9 H11 N4 O4 S1'
_chemical_oxdiff_usercomment     'colourless plate, Cu, 100K, 0.20x0.10x0.03'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C9(H9), C10(H10)
;
_shelx_res_checksum              10707
_shelx_hkl_checksum              23135
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.757