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_1572513
_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         'C4 H6 N7, C6 H3 N2 O4, C4 H5 N7, 1.5(H2 O)'
_chemical_formula_sum            'C14 H17 N16 O5.5'
_chemical_formula_weight         497.43
_chemical_name_systematic
;
'2,6-diamino-5-azapurin-9-ium 3-carboxypyrazine-2-carboxylate 
2,6-diamino-5-azapurine sesquihydrate'
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-06-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.307(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.7740(5)
_cell_length_b                   6.56343(9)
_cell_length_c                   26.4567(5)
_cell_measurement_reflns_used    15759
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      70.0380
_cell_measurement_theta_min      3.4320
_cell_volume                     4012.05(16)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 16.0131
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_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    -36.00  42.00   1.00    1.00    --    0.00  77.00 -90.00   78
  2  \w    -27.00  73.00   1.00    1.00    --    0.00  57.00-180.00  100
  3  \w    -21.00  36.00   1.00    1.00    --    0.00 -77.00-150.00   57
  4  \w    -84.00 -39.00   1.00    1.00    --    0.00-178.00   0.00   45
  5  \w    -87.00  -6.00   1.00    3.60    --  -53.50 125.00 -60.00   81
  6  \w   -128.00 -76.00   1.00    3.60    --  -53.50-125.00   0.00   52
  7  \w   -128.00 -76.00   1.00    3.60    --  -53.50-125.00-180.00   52
  8  \w   -128.00 -76.00   1.00    3.60    --  -53.50-125.00 120.00   52
  9  \w   -131.00 -83.00   1.00    3.60    --  -53.50 -93.00 -90.00   48
 10  \w   -128.00 -76.00   1.00    3.60    --  -53.50-125.00 -90.00   52
 11  \w   -125.00 -26.00   1.00    3.60    --  -53.50 -61.00-150.00   99
 12  \w   -128.00 -76.00   1.00    3.60    --  -53.50-125.00  30.00   52
 13  \w   -131.00  -6.00   1.00    3.60    --  -53.50 -30.00  90.00  125
 14  \w      1.00 101.00   1.00    3.60    --   56.00 -94.00 -60.00  100
 15  \w      1.00 101.00   1.00    3.60    --   56.00 -94.00  90.00  100
 16  \w      1.00 101.00   1.00    3.60    --   56.00 -94.00-150.00  100
 17  \w     36.00 149.00   1.00    6.00    --  112.00 -37.00 -90.00  113
 18  \w    103.00 178.00   1.00    6.00    --  112.00  77.00-120.00   75
 19  \w     61.00 146.00   1.00    6.00    --  112.00 178.00  60.00   85
 20  \w     35.00 107.00   1.00    6.00    --  112.00 -91.00 150.00   72
 21  \w     61.00 146.00   1.00    6.00    --  112.00 178.00  90.00   85
 22  \w     36.00 109.00   1.00    6.00    --  112.00-111.00 -90.00   73
 23  \w     40.00 140.00   1.00    6.00    --  112.00 -63.00-180.00  100
 24  \w     84.00 178.00   1.00    6.00    --  112.00  63.00 -90.00   94
 25  \w     36.00 109.00   1.00    6.00    --  112.00-111.00  60.00   73
 26  \w     84.00 178.00   1.00    6.00    --  112.00  63.00-150.00   94
 27  \w     38.00 142.00   1.00    6.00    --  112.00 -50.00 120.00  104
 28  \w     36.00 109.00   1.00    6.00    --  112.00-111.00  90.00   73
 29  \w     61.00 146.00   1.00    6.00    --  112.00 178.00  30.00   85
 30  \w     61.00 146.00   1.00    6.00    --  112.00 178.00 150.00   85
 31  \w     35.00 107.00   1.00    6.00    --  112.00 -91.00  90.00   72
 32  \w     37.00 178.00   1.00    6.00    --  112.00  12.00-150.00  141
 33  \w    -84.00 -39.00   1.00    1.00    --    0.00-178.00 -90.00   45
 34  \w    -84.00 -39.00   1.00    1.00    --    0.00-178.00-150.00   45
 35  \w     -1.00  45.00   1.00    1.00    --    0.00 -93.00 -90.00   46
 36  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -74.00 -69.58  107
 37  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -74.00  32.31  107
 38  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -73.00  -1.46  107
 39  \w   -126.00 -21.00   1.00    3.60    --  -53.50 -71.00  62.52  105
 40  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -73.00 174.64  107
 41  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -73.00-110.51  107
 42  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -73.00 -48.05  107
 43  \w   -127.00 -20.00   1.00    3.60    --  -53.50 -73.00 123.95  107
 44  \w     24.00 131.00   1.00    3.60    --   56.00  45.00   0.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.048
_diffrn_reflns_theta_min         3.727
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81975
_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    1.647
_exptl_crystal_description       block
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+4.1556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3632
_reflns_number_total             3775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k7a7
_cod_original_cell_volume        4012.05(15)
_cod_original_formula_sum        'C14 H17 N16 O5.50'
_cod_database_code               1572513
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups
2. Restrained distances
 O4-H4
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C14(H14), C10(H10)
;
_shelx_res_checksum              1880
_shelx_hkl_checksum              45974
_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
;