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_1572510
_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 N2 O4, C4 H7 N4, H2 O'
_chemical_formula_sum            'C10 H12 N6 O5'
_chemical_formula_weight         296.26
_chemical_name_systematic
' 2,4-diaminopyrimidin-1-ium  3-carboxypyrazine-2-carboxylate monohydrate'
_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                 92.4078(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.54619(5)
_cell_length_b                   12.52881(9)
_cell_length_c                   15.12082(15)
_cell_measurement_reflns_used    22894
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      69.6720
_cell_measurement_theta_min      4.5550
_cell_volume                     1239.054(18)
_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 0.996
_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    -32.00  42.00   1.00    1.00    --    0.00  77.00-150.00   74
  2  \w    -21.00  32.00   1.00    1.00    --    0.00 -77.00   0.00   53
  3  \w    -22.00  69.00   1.00    1.00    --    0.00  57.00 -30.00   91
  4  \w    -21.00  32.00   1.00    1.00    --    0.00 -77.00-120.00   53
  5  \w     30.00 122.00   1.00    1.75    --   54.00  62.00 -48.31   92
  6  \w     25.00 124.00   1.00    1.75    --   54.00  72.00  74.76   99
  7  \w     26.00 124.00   1.00    1.75    --   54.00  70.00 179.45   98
  8  \w     32.00 123.00   1.00    1.75    --   54.00  57.00-180.00   91
  9  \w     32.00 123.00   1.00    1.75    --   54.00  57.00 -60.00   91
 10  \w      6.00  98.00   1.00    1.75    --   54.00 -99.00 120.00   92
 11  \w     25.00 124.00   1.00    1.75    --   54.00  72.00 116.94   99
 12  \w     32.00 123.00   1.00    1.75    --   54.00  57.00 -90.00   91
 13  \w    -19.00  81.00   1.00    1.75    --   54.00 -37.00 120.00  100
 14  \w     32.00 123.00   1.00    1.75    --   54.00  57.00-120.00   91
 15  \w     26.00 124.00   1.00    1.75    --   54.00  70.00 -26.63   98
 16  \w    -17.00  86.00   1.00    1.75    --   54.00 -77.00 -60.00  103
 17  \w     32.00 123.00   1.00    1.75    --   54.00  57.00  30.00   91
 18  \w    -19.00  81.00   1.00    1.75    --   54.00 -37.00 -30.00  100
 19  \w     26.00 124.00   1.00    1.75    --   54.00  70.00  36.40   98
 20  \w    -17.00  86.00   1.00    1.75    --   54.00 -77.00 -90.00  103
 21  \w     35.00 109.00   1.00    2.50    --  108.00-111.00 -60.00   74
 22  \w     80.00 178.00   1.00    2.50    --  108.00  71.00  10.79   98
 23  \w     85.00 178.00   1.00    2.50    --  108.00  50.00   0.00   93
 24  \w     84.00 175.00   1.00    2.50    --  108.00  63.00-180.00   91
 25  \w     86.00 177.00   1.00    2.50    --  108.00  59.00 -77.96   91
 26  \w     35.00 106.00   1.00    2.50    --  108.00 -91.00 150.00   71
 27  \w     85.00 178.00   1.00    2.50    --  108.00  50.00-120.00   93
 28  \w     83.00 176.00   1.00    2.50    --  108.00  65.00-145.59   93
 29  \w     84.00 175.00   1.00    2.50    --  108.00  63.00  90.00   91
 30  \w     84.00 175.00   1.00    2.50    --  108.00  63.00 -90.00   91
 31  \w     81.00 178.00   1.00    2.50    --  108.00  69.00-115.45   97
 32  \w     35.00 135.00   1.00    2.50    --  108.00 -37.00 -90.00  100
 33  \w     85.00 178.00   1.00    2.50    --  108.00  50.00-180.00   93
 34  \w     85.00 178.00   1.00    2.50    --  108.00  50.00  90.00   93
 35  \w     84.00 175.00   1.00    2.50    --  108.00  63.00   0.00   91
 36  \w     85.00 178.00   1.00    2.50    --  108.00  50.00 -30.00   93
 37  \w     84.00 175.00   1.00    2.50    --  108.00  63.00-120.00   91
 38  \w     84.00 175.00   1.00    2.50    --  108.00  63.00 -30.00   91
 39  \w     85.00 178.00   1.00    2.50    --  108.00  50.00-150.00   93
 40  \w     41.00 132.00   1.00    2.50    --  108.00 -63.00-180.00   91
 41  \w     77.00 178.00   1.00    2.50    --  108.00  33.00 -59.45  101
 42  \w     84.00 175.00   1.00    2.50    --  108.00  63.00  60.00   91
 43  \w     85.00 178.00   1.00    2.50    --  108.00  50.00 120.00   93
 44  \w     35.00 109.00   1.00    2.50    --  108.00-111.00  60.00   74
 45  \w     35.00 109.00   1.00    2.50    --  108.00-111.00-150.00   74
 46  \w     84.00 175.00   1.00    2.50    --  108.00  63.00  30.00   91
 47  \w     84.00 175.00   1.00    2.50    --  108.00  63.00 150.00   91
 48  \w     84.00 178.00   1.00    2.50    --  108.00  46.00 149.00   94
 49  \w     84.00 175.00   1.00    2.50    --  108.00  63.00-150.00   91
 50  \w     35.00 106.00   1.00    2.50    --  108.00 -91.00 -30.00   71
 51  \w     35.00 106.00   1.00    2.50    --  108.00 -91.00  90.00   71
 52  \w     85.00 178.00   1.00    2.50    --  108.00  50.00  60.00   93
 53  \w     84.00 175.00   1.00    2.50    --  108.00  63.00 -60.00   91
 54  \w     85.00 178.00   1.00    2.50    --  108.00  50.00 -60.00   93
 55  \w     81.00 178.00   1.00    2.50    --  108.00  37.00-180.00   97
 56  \w     84.00 175.00   1.00    2.50    --  108.00  63.00 120.00   91
 57  \w    -74.00  74.00   1.00    1.00    --    0.00   0.00-180.00  148
 58  \w    -73.00  27.00   1.00    1.00    --    0.00 -37.00 150.00  100
 59  \w    -74.00  74.00   1.00    1.00    --    0.00   0.00-120.00  148
 60  \w    -74.00  74.00   1.00    1.00    --    0.00   0.00-150.00  148
 61  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00 -90.00  148
 62  \w     28.00 123.00   1.00    1.75    --   54.00  66.00 116.97   95
 63  \w     32.00 124.00   1.00    1.75    --   54.00  54.00 -89.77   92
 64  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00-150.00  148
 65  \w     32.00 123.00   1.00    1.75    --   54.00  57.00 -30.00   91
 66  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00-120.00  148
 67  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00-180.00  148
 68  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00 -60.00  148
 69  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00 -30.00  148
 70  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00   0.00  148
 71  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00  60.00  148
 72  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00  30.00  148
 73  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00  90.00  148
 74  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00 120.00  148
 75  \w    -20.00 128.00   1.00    1.75    --   54.00   0.00 150.00  148
 76  \w    -20.00 112.00   1.00    1.75    --   54.00   0.00-180.00  132
 77  \w     27.00 112.00   1.00    1.75    --   54.00-125.00-120.00   85
;
_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      -0.2078514000
_diffrn_orient_matrix_UB_12      0.0562211000
_diffrn_orient_matrix_UB_13      -0.0150766000
_diffrn_orient_matrix_UB_21      -0.0786710000
_diffrn_orient_matrix_UB_22      -0.0952871000
_diffrn_orient_matrix_UB_23      -0.0561354000
_diffrn_orient_matrix_UB_31      -0.0780383000
_diffrn_orient_matrix_UB_32      -0.0536677000
_diffrn_orient_matrix_UB_33      0.0837825000
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38635
_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         69.591
_diffrn_reflns_theta_min         4.585
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72297
_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    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0330P)^2^+0.7476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2182
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k7a2
_cod_database_code               1572510
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C10 H10 N6 O4'
_chemical_oxdiff_usercomment     'colourless block, Cu, 100K, 0.20x0.14x0.07'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H,H,H,H) groups
 At 1.5 times of:
  All O(H,H,H) groups
2. Restrained distances
 O4-H4
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C4(H4A), C10(H10)
;
_shelx_res_checksum              91114
_shelx_hkl_checksum              35490
_olex2_date_sample_data_collection 2021-02-14
_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.769