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_1572512
_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, C5 H7 N6'
_chemical_formula_sum            'C11 H10 N8 O4'
_chemical_formula_weight         318.27
_chemical_name_systematic
'2,6-diaminopurin-1-ium 3-carboxypyrazine-2-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                 108.486(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3148(2)
_cell_length_b                   14.8388(3)
_cell_length_c                   9.4812(3)
_cell_measurement_reflns_used    8645
_cell_measurement_temperature    129.5(1)
_cell_measurement_theta_max      70.5270
_cell_measurement_theta_min      2.9620
_cell_volume                     1242.88(6)
_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      129.5(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 0.993
_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  16.00   1.00    1.00    --    0.00  54.00-148.00   37
  2  \w    -69.00  -2.00   1.00    1.00    --    0.00 -54.00  67.00   67
  3  \w     36.00  65.00   1.00    1.00    --    0.00  54.00-148.00   29
  4  \w    -34.00  -7.00   1.00    1.00    --   14.00 110.00-126.13   27
  5  \w     -4.00  22.00   1.00    1.00    --   34.00  91.00-121.10   26
  6  \w      1.00  26.00   1.00    1.00    --   38.00  90.00  59.03   25
  7  \w     15.00  42.00   1.00    1.00    --   46.00  80.00   5.31   27
  8  \w     14.00  41.00   1.00    1.00    --   46.00  82.00 122.22   27
  9  \w     15.00  42.00   1.00    1.00    --   46.00  80.00 -52.20   27
 10  \w     14.00  39.00   1.00    1.00    --   46.00  80.00-156.52   25
 11  \w     22.00  48.00   1.00    1.00    --   50.00  73.00 -97.94   26
 12  \w     77.00 119.00   1.00    1.00    --   50.00  73.00 -97.94   42
 13  \w     28.00  76.00   1.00    1.00    --   54.00-125.00 -90.00   48
 14  \w     28.00  72.00   1.00    1.00    --   54.00  74.00  57.90   44
 15  \w     76.00 123.00   1.00    1.00    --   54.00  71.00 155.23   47
 16  \w     30.00  68.00   1.00    1.00    --   54.00  71.00 155.23   38
 17  \w     80.00 122.00   1.00    1.00    --   54.00  74.00  57.90   42
 18  \w     50.00  75.00   1.00    1.00    --   54.00 -57.00  30.00   25
 19  \w     27.00  89.00   1.00    1.00    --   54.00-125.00-180.00   62
 20  \w    -14.00  44.00   1.00    1.00    --   54.00 -57.00  30.00   58
 21  \w      6.00  76.00   1.00    1.00    --   54.00 -99.00 -30.00   70
 22  \w     31.00  57.00   1.00    1.00    --   58.00  72.00  -5.96   26
 23  \w    103.00 128.00   1.00    1.00    --   58.00  74.00-158.88   25
 24  \w     32.00  62.00   1.00    1.00    --   58.00  74.00-158.88   30
 25  \w     35.00  60.00   1.00    1.00    --   58.00  72.00 -77.93   25
 26  \w     31.00  57.00   1.00    1.00    --   58.00  74.00-100.80   26
 27  \w     34.00  71.00   1.00    1.00    --   62.00  73.00  80.06   37
 28  \w     43.00  69.00   1.00    1.00    --   62.00  60.00 -84.59   26
 29  \w    103.00 131.00   1.00    1.00    --   62.00  73.00  80.06   28
 30  \w    106.00 135.00   1.00    1.00    --   66.00  53.00 -65.25   29
 31  \w     45.00  77.00   1.00    1.00    --   66.00  53.00 -65.25   32
 32  \w    110.00 135.00   1.00    1.00    --   66.00  58.00-171.49   25
 33  \w     46.00  71.00   1.00    1.00    --   66.00  58.00-171.49   25
 34  \w     99.00 137.00   1.00    1.00    --   70.00  62.00 -36.00   38
 35  \w     48.00  73.00   1.00    1.00    --   70.00  62.00 -36.00   25
 36  \w     56.00  84.00   1.00    1.00    --   70.00  51.00 132.09   28
 37  \w    115.00 141.00   1.00    1.00    --   74.00  68.00 -26.41   26
 38  \w     50.00  78.00   1.00    1.00    --   74.00  68.00 -26.41   28
 39  \w     60.00  85.00   1.00    1.00    --   82.00  48.00 119.26   25
 40  \w     55.00  92.00   1.00    1.00    --   82.00  71.00  -4.95   37
 41  \w     58.00 149.00   1.00    1.00    --   82.00  67.00  19.96   91
 42  \w     64.00  90.00   1.00    1.00    --   86.00  62.00  72.27   26
 43  \w     64.00  97.00   1.00    1.00    --   86.00  62.00-151.76   33
 44  \w     74.00 100.00   1.00    1.00    --  102.00  74.00 115.49   26
 45  \w    107.00 161.00   1.00    1.00    --  102.00  74.00 115.49   54
 46  \w     80.00 106.00   1.00    1.00    --  108.00  74.00-130.31   26
 47  \w     86.00 112.00   1.00    1.00    --  108.00  50.00   0.00   26
 48  \w    153.00 178.00   1.00    1.00    --  108.00  50.00-180.00   25
 49  \w     87.00 121.00   1.00    1.00    --  108.00  50.00-180.00   34
 50  \w    107.00 163.00   1.00    1.00    --  108.00 111.00 120.00   56
 51  \w     93.00 123.00   1.00    1.00    --  108.00 -50.00-150.00   30
 52  \w     39.00  89.00   1.00    1.00    --  108.00 -50.00-150.00   50
 53  \w     86.00 119.00   1.00    1.00    --  108.00  45.00  56.69   33
 54  \w     86.00 112.00   1.00    1.00    --  108.00  50.00 -90.00   26
 55  \w     87.00 170.00   1.00    1.00    --  108.00  63.00 -60.00   83
 56  \w     86.00 151.00   1.00    1.00    --  108.00  63.00-150.00   65
 57  \w     44.00 130.00   1.00    1.00    --  108.00 -63.00  90.00   86
 58  \w     72.00 105.00   1.00    1.00    --  108.00 -91.00 -60.00   33
 59  \w    141.00 167.00   1.00    1.00    --  108.00  63.00   0.00   26
 60  \w     86.00 111.00   1.00    1.00    --  108.00  63.00   0.00   25
 61  \w     88.00 115.00   1.00    1.00    --  108.00  50.00  30.00   27
 62  \w    119.00 168.00   1.00    1.00    --  108.00  50.00  30.00   49
 63  \w     88.00 125.00   1.00    1.00    --  108.00  63.00-180.00   37
 64  \w     74.00 104.00   1.00    1.00    --  108.00 -91.00-180.00   30
 65  \w     72.00 107.00   1.00    1.00    --  108.00-111.00  90.00   35
 66  \w     37.00  65.00   1.00    1.00    --  108.00-111.00  90.00   28
 67  \w     86.00 124.00   1.00    1.00    --  108.00  63.00 -90.00   38
 68  \w     80.00 107.00   1.00    1.00    --  108.00 -91.00  90.00   27
 69  \w    122.00 148.00   1.00    1.00    --  108.00  50.00 120.00   26
 70  \w     66.00 107.00   1.00    1.00    --  108.00 -91.00-120.00   41
 71  \w     87.00 112.00   1.00    1.00    --  108.00  50.00 120.00   25
 72  \w     86.00 116.00   1.00    1.00    --  108.00  50.00 -60.00   30
 73  \w     37.00  62.00   1.00    1.00    --  108.00 -91.00-120.00   25
 74  \w     37.00  62.00   1.00    1.00    --  108.00 -91.00  90.00   25
 75  \w     88.00 155.00   1.00    1.00    --  108.00  63.00  60.00   67
 76  \w    106.00 178.00   1.00    1.00    --  108.00 111.00 150.00   72
 77  \w    129.00 173.00   1.00    1.00    --  108.00  63.00 -90.00   44
 78  \w     86.00 111.00   1.00    1.00    --  108.00  63.00 150.00   25
 79  \w     82.00 173.00   1.00    1.00    --  108.00  71.00  78.32   91
 80  \w     87.00 170.00   1.00    1.00    --  108.00  52.00 -23.88   83
 81  \w     86.00 113.00   1.00    1.00    --  108.00  50.00 150.00   27
 82  \w    122.00 174.00   1.00    1.00    --  108.00  74.00-130.31   52
;
_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      0.0007985000
_diffrn_orient_matrix_UB_12      0.0511127000
_diffrn_orient_matrix_UB_13      0.1417594000
_diffrn_orient_matrix_UB_21      0.1527065000
_diffrn_orient_matrix_UB_22      -0.0438885000
_diffrn_orient_matrix_UB_23      0.0856430000
_diffrn_orient_matrix_UB_31      0.0842036000
_diffrn_orient_matrix_UB_32      0.0790049000
_diffrn_orient_matrix_UB_33      -0.0439346000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17622
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.395
_diffrn_reflns_theta_min         5.753
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81449
_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    1.701
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0586P)^2^+0.5789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2211
_reflns_number_total             2368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k7a6
_cod_original_cell_volume        1242.87(6)
_cod_database_code               1572512
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H10 N8 O4'
_chemical_oxdiff_usercomment     'colourless block, Cu, 129.6K, 0.18x0.120x0.09'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N3-H3
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C3(H3A)
;
_shelx_res_checksum              81774
_shelx_hkl_checksum              90086
_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.715