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_1572511
_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 H6 Cl N4'
_chemical_formula_sum            'C10 H9 Cl N6 O4'
_chemical_formula_weight         312.68
_chemical_name_systematic
'2,4-diamino-6-chloropyrimidin-3-ium 3-carboxypyrazine-2-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 112.3165(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.83584(14)
_cell_length_b                   15.2908(2)
_cell_length_c                   8.52118(14)
_cell_measurement_reflns_used    11478
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      69.7990
_cell_measurement_theta_min      5.6480
_cell_volume                     1185.58(3)
_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 0.994
_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    -22.00  69.00   1.00    1.00    --    0.00  57.00 150.00   91
  2  \w    -69.00  22.00   1.00    1.00    --    0.00 -57.00   0.00   91
  3  \w    -27.00  10.00   1.00    1.00    --   20.00 106.00  -0.83   37
  4  \w     -4.00  23.00   1.00    1.50    --   36.00  92.00 165.04   27
  5  \w      1.00  29.00   1.00    1.50    --   40.00  90.00-164.22   28
  6  \w     10.00  42.00   1.00    1.50    --   44.00  82.00  65.70   32
  7  \w     14.00  42.00   1.00    1.50    --   48.00  81.00-151.70   28
  8  \w     14.00  42.00   1.00    1.50    --   48.00  81.00 145.96   28
  9  \w     15.00  42.00   1.00    1.50    --   48.00  80.00 -30.98   27
 10  \w     14.00  42.00   1.00    1.50    --   48.00  82.00 -93.09   28
 11  \w     16.00  42.00   1.00    1.50    --   48.00  77.00  21.48   26
 12  \w      6.00  98.00   1.00    1.50    --   54.00 -99.00 -60.00   92
 13  \w     32.00 123.00   1.00    1.50    --   54.00  57.00  90.00   91
 14  \w     32.00 123.00   1.00    1.50    --   54.00  57.00   0.00   91
 15  \w    -15.00  76.00   1.00    1.50    --   54.00 -57.00 150.00   91
 16  \w      6.00  98.00   1.00    1.50    --   54.00 -99.00 120.00   92
 17  \w    -15.00  76.00   1.00    1.50    --   54.00 -57.00   0.00   91
 18  \w     30.00 125.00   1.00    1.50    --   56.00  67.00-132.12   95
 19  \w     35.00 128.00   1.00    1.50    --   60.00  65.00 -75.16   93
 20  \w     35.00 134.00   1.00    1.50    --   64.00  73.00-166.39   99
 21  \w     42.00 133.00   1.00    1.50    --   64.00  56.00 110.64   91
 22  \w     44.00 136.00   1.00    1.50    --   68.00  62.00 106.26   92
 23  \w     44.00 136.00   1.00    1.50    --   68.00  62.00  32.17   92
 24  \w     47.00 140.00   1.00    1.50    --   72.00  64.00 160.51   93
 25  \w     50.00 142.00   1.00    1.50    --   72.00  53.00  10.08   92
 26  \w     46.00 141.00   1.00    1.50    --   72.00  66.00  33.76   95
 27  \w     49.00 146.00   1.00    1.50    --   76.00  69.00 123.22   97
 28  \w     58.00 150.00   1.00    1.50    --   80.00  53.00-111.45   92
 29  \w     57.00 148.00   1.00    1.50    --   80.00  61.00-155.73   91
 30  \w     50.00 150.00   1.00    1.50    --   80.00  74.00 -93.88  100
 31  \w     74.00 169.00   1.00    2.00    --  100.00  67.00-169.28   95
 32  \w    104.00 178.00   1.00    2.00    --  108.00 111.00-150.00   74
 33  \w     85.00 178.00   1.00    2.00    --  108.00  50.00   0.00   93
 34  \w     85.00 178.00   1.00    2.00    --  108.00  50.00 150.00   93
 35  \w     85.00 178.00   1.00    2.00    --  108.00  50.00  90.00   93
 36  \w     35.00 106.00   1.00    2.00    --  108.00 -91.00 -30.00   71
 37  \w     35.00 109.00   1.00    2.00    --  108.00-111.00-180.00   74
 38  \w     84.00 175.00   1.00    2.00    --  108.00  63.00  30.00   91
 39  \w     84.00 175.00   1.00    2.00    --  108.00  63.00 -90.00   91
 40  \w     84.00 175.00   1.00    2.00    --  108.00  63.00-150.00   91
 41  \w     84.00 175.00   1.00    2.00    --  108.00  63.00 -60.00   91
 42  \w     41.00 132.00   1.00    2.00    --  108.00 -63.00  90.00   91
 43  \w     84.00 175.00   1.00    2.00    --  108.00  63.00 -30.00   91
 44  \w     84.00 175.00   1.00    2.00    --  108.00  63.00 150.00   91
 45  \w     84.00 175.00   1.00    2.00    --  108.00  63.00 120.00   91
 46  \w     41.00 102.00   1.00    2.00    --  108.00 -91.00  60.00   61
 47  \w     86.00 111.00   1.00    2.00    --  108.00  50.00-120.00   25
 48  \w     35.00  65.00   1.00    2.00    --  108.00 -91.00  30.00   30
 49  \w     85.00 175.00   1.00    2.00    --  108.00  63.00  60.00   90
 50  \w     85.00 118.00   1.00    2.00    --  108.00  50.00  60.00   33
 51  \w     84.00 165.00   1.00    2.00    --  108.00  63.00   0.00   81
 52  \w     84.00 174.00   1.00    2.00    --  108.00  63.00-120.00   90
 53  \w     36.00 109.00   1.00    2.00    --  108.00-111.00 -60.00   73
 54  \w     35.00  82.00   1.00    2.00    --  108.00 -91.00-120.00   47
 55  \w     85.00 178.00   1.00    2.00    --  108.00  50.00-180.00   93
 56  \w     86.00 118.00   1.00    2.00    --  108.00  50.00  30.00   32
 57  \w     84.00 166.00   1.00    2.00    --  108.00  63.00  90.00   82
 58  \w     86.00 114.00   1.00    2.00    --  108.00  50.00 -30.00   28
 59  \w     85.00 117.00   1.00    2.00    --  108.00  50.00 -60.00   32
;
_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      0.1524582000
_diffrn_orient_matrix_UB_12      -0.0341169000
_diffrn_orient_matrix_UB_13      0.0173331000
_diffrn_orient_matrix_UB_21      0.0659119000
_diffrn_orient_matrix_UB_22      0.0347046000
_diffrn_orient_matrix_UB_23      0.1833708000
_diffrn_orient_matrix_UB_31      -0.0330138000
_diffrn_orient_matrix_UB_32      -0.0881976000
_diffrn_orient_matrix_UB_33      0.0653388000
_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  0.0302
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.922
_diffrn_reflns_theta_min         4.860
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69598
_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    1.752
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0344P)^2^+0.6828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2118
_reflns_number_total             2237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            structures_1-7.cif
_cod_data_source_block           k7a3
_cod_database_code               1572511
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C10 H9 N6 O4 Cl1'
_chemical_oxdiff_usercomment     'colourless block, Cu, 100K, 0.20x0.12x0.04'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C3(H3A)
;
_shelx_res_checksum              54847
_shelx_hkl_checksum              2216
_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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.741