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_7245651
_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, 0.5(H2 O)'
_chemical_formula_sum            'C10 H8 N O6.5'
_chemical_formula_weight         246.17
_chemical_melting_point          547
_chemical_name_common
'3-carboxypyridinium hydrogen squarate hemihydrate'
_chemical_name_systematic        'nicotinium hydrogen squarate hemihydrate'
_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             2021-06-10
_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                68.313(14)
_cell_angle_beta                 78.335(11)
_cell_angle_gamma                74.819(12)
_cell_formula_units_Z            4
_cell_length_a                   9.7193(11)
_cell_length_b                   9.8781(16)
_cell_length_c                   11.6443(16)
_cell_measurement_reflns_used    2382
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.1950
_cell_measurement_theta_min      3.3900
_cell_volume                     995.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_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    -86.00   4.00   1.00   16.50    --  -17.27 -57.00 -60.00   90
  2  \w    -39.00   4.00   1.00   16.50    --  -17.27 -77.00 120.00   43
  3  \w    -38.00  48.00   1.00   16.50    --  -17.27  57.00-150.00   86
  4  \w    -10.00  16.00   1.00   16.50    --  -17.27 -99.00 -30.00   26
  5  \w    -22.00   9.00   1.00   16.50    --  -17.27 -77.00-150.00   31
  6  \w    -39.00  52.00   1.00   16.50    --  -17.27  57.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0403986000
_diffrn_orient_matrix_UB_12      -0.0519763000
_diffrn_orient_matrix_UB_13      0.0481770000
_diffrn_orient_matrix_UB_21      0.0632757000
_diffrn_orient_matrix_UB_22      0.0016818000
_diffrn_orient_matrix_UB_23      -0.0429100000
_diffrn_orient_matrix_UB_31      0.0127374000
_diffrn_orient_matrix_UB_32      0.0594198000
_diffrn_orient_matrix_UB_33      0.0139737000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.562
_diffrn_reflns_theta_min         3.058
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.642
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol-water'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0525P)^2^+0.0766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3247
_reflns_number_total             4246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00760f2.cif
_cod_data_source_block           mg_nica-sqa
_cod_depositor_comments
;

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H16 N2 O13'
_cod_original_formula_weight         492.35
_cod_original_formula_moiety         '2(C4 H O4), 2(C6 H6 N O2), H2 O'
_cod_original_formula_units_Z            2
_cod_database_code               7245651
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H16 N2 O13'
_chemical_oxdiff_usercomment     '0.19 x 0.20 x 0.38 block, 100K'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.948
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
;
_shelx_res_checksum              89827
_shelx_hkl_checksum              72387
_olex2_date_sample_data_collection 2020-07-13
_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 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.942
_publcif_funding_html
;
;