Synthesis and structural characteristic of pyridine carboxylic acids adducts with squaric acid
Gołdyn, Mateusz; Skowronek, Julia; Komasa, Anna; Bartoszak-Adamska, Elżbieta; Lewandowska, Aneta; Dega-Szafran, Zofia; Cofta, Grzegorz; CrystEngComm  (2022) –; doi:10.1039/D2CE00760F

data_7245652
_publ_section_title
;
 Synthesis and structural characteristic of pyridine carboxylic acids
 adducts with squaric acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00760F
_journal_year                    2022
_chemical_formula_moiety         'C4 H O4, C6 H6 N O2'
_chemical_formula_sum            'C10 H7 N O6'
_chemical_formula_weight         237.17
_chemical_melting_point          552
_chemical_name_common            '4-carboxypyridinium hydrogen squarate'
_chemical_name_systematic        'isonicotinium hydrogen squarate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-09
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-12-14 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                82.366(4)
_cell_angle_beta                 77.224(3)
_cell_angle_gamma                78.515(4)
_cell_formula_units_Z            4
_cell_length_a                   6.5246(2)
_cell_length_b                   11.8093(6)
_cell_length_c                   12.8138(5)
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    134.6(2)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      3.5200
_cell_volume                     939.51(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      134.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_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    -94.00 -39.00   1.00    1.00    --  -41.23 125.00  60.00   55
  2  \w    -71.00 -15.00   1.00    1.00    --  -41.23 125.00-180.00   56
  3  \w     24.00  71.00   1.00    1.00    --   41.23-125.00   0.00   47
  4  \w    -39.00  26.00   1.00    1.00    --   41.23 -19.00 -30.00   65
  5  \w      0.00 121.00   1.00    1.00    --   41.23  19.00 150.00  121
  6  \w     78.00 104.00   1.00    5.00    --  112.00 -94.00-120.00   26
  7  \w     85.00 146.00   1.00    5.00    --  112.00  30.00 -30.00   61
  8  \w     42.00  69.00   1.00    5.00    --  112.00 -61.00-120.00   27
  9  \w     40.00  70.00   1.00    5.00    --  112.00 -61.00   0.00   30
 10  \w     61.00  87.00   1.00    5.00    --  112.00-111.00-180.00   26
 11  \w     90.00 158.00   1.00    5.00    --  112.00  15.00-180.00   68
 12  \w     40.00  67.00   1.00    5.00    --  112.00 -61.00 -60.00   27
 13  \w     70.00 109.00   1.00    5.00    --  112.00-111.00 -60.00   39
 14  \w     84.00 155.00   1.00    5.00    --  112.00  61.00-180.00   71
 15  \w     83.00 145.00   1.00    5.00    --  112.00  61.00  60.00   62
 16  \w     42.00  67.00   1.00    5.00    --  112.00 -61.00 -90.00   25
 17  \w    112.00 142.00   1.00    5.00    --  112.00  77.00  30.00   30
 18  \w     46.00  71.00   1.00    5.00    --  112.00 -61.00-150.00   25
 19  \w    105.00 131.00   1.00    5.00    --  112.00 179.00-150.00   26
 20  \w     75.00 109.00   1.00    5.00    --  112.00-111.00 -30.00   34
 21  \w     43.00 109.00   1.00    5.00    --  112.00-111.00-150.00   66
 22  \w     59.00  86.00   1.00    5.00    --  112.00  15.00-180.00   27
 23  \w     73.00 109.00   1.00    5.00    --  112.00-111.00  60.00   36
 24  \w     80.00 105.00   1.00    5.00    --  112.00 -94.00  60.00   25
 25  \w     50.00  94.00   1.00    5.00    --  112.00 179.00-150.00   44
 26  \w     84.00 158.00   1.00    5.00    --  112.00  30.00 -90.00   74
 27  \w     41.00  68.00   1.00    5.00    --  112.00 -61.00  60.00   27
 28  \w     79.00 105.00   1.00    5.00    --  112.00-111.00 150.00   26
 29  \w    112.00 157.00   1.00    5.00    --  112.00  30.00  30.00   45
 30  \w     41.00  67.00   1.00    5.00    --  112.00 -61.00-180.00   26
 31  \w     40.00  68.00   1.00    5.00    --  112.00 -61.00  90.00   28
 32  \w     42.00  68.00   1.00    5.00    --  112.00 -61.00 120.00   26
 33  \w     85.00 127.00   1.00    5.00    --  112.00 179.00 -30.00   42
 34  \w     68.00  97.00   1.00    5.00    --  112.00 -77.00  30.00   29
 35  \w     95.00 120.00   1.00    5.00    --  112.00  45.00   0.00   25
 36  \w     36.00 102.00   1.00    5.00    --  112.00-111.00  30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1953204000
_diffrn_orient_matrix_UB_12      0.0267598000
_diffrn_orient_matrix_UB_13      -0.0539611000
_diffrn_orient_matrix_UB_21      -0.0298805000
_diffrn_orient_matrix_UB_22      0.1290281000
_diffrn_orient_matrix_UB_23      0.0185126000
_diffrn_orient_matrix_UB_31      0.1464217000
_diffrn_orient_matrix_UB_32      0.0225963000
_diffrn_orient_matrix_UB_33      -0.1098896000
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.446
_diffrn_reflns_theta_min         3.552
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile-water'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0827P)^2^+0.1046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3378
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00760f2.cif
_cod_data_source_block           mg-red-sqa-izonica
_cod_database_code               7245652
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H7N1O6
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.748
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              24896
_shelx_hkl_checksum              70121
_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_publcif_funding_html
;
;