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_7245653
_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          536
_chemical_name_common            '2-carboxypyridinium hydrogen squarate'
_chemical_name_systematic        'picolinium hydrogen squarate'
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-27
_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                90
_cell_angle_beta                 115.211(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2508(9)
_cell_length_b                   16.8024(9)
_cell_length_c                   11.2451(9)
_cell_measurement_reflns_used    6829
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.3210
_cell_measurement_theta_min      3.7600
_cell_volume                     1923.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXS  (Sheldrick, 2008)'
_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 0.860
_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     -2.00  75.00   1.00   10.00    --   16.56-126.00 102.00   77
  2  \w    -13.00  87.00   1.00   10.00    --   16.56  77.00   0.00  100
  3  \w    -25.00  58.00   1.00   10.00    --   16.56 -99.00-180.00   83
  4  \w     -9.00  89.00   1.00   10.00    --   16.56  37.00 -30.00   98
  5  \w    -75.00   2.00   1.00   10.00    --  -17.35 126.00-179.00   77
  6  \w    -86.00   4.00   1.00   10.00    --  -17.35 -57.00  60.00   90
  7  \w    -38.00  51.00   1.00   10.00    --  -17.35  57.00 -30.00   89
  8  \w    -38.00  51.00   1.00   10.00    --  -17.35  57.00-120.00   89
  9  \w    -86.00   4.00   1.00   10.00    --  -17.35 -57.00-180.00   90
 10  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00-120.00  146
 11  \w    -25.00  58.00   1.00   10.00    --   16.56 -99.00 -30.00   83
 12  \w    -25.00  58.00   1.00   10.00    --   16.56 -99.00  90.00   83
 13  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00-180.00  146
 14  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00-150.00  146
 15  \w    -38.00  51.00   1.00   10.00    --  -17.35  57.00-180.00   89
 16  \w    -25.00  25.00   1.00   10.00    --  -17.35 -99.00  90.00   50
 17  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00 -60.00  146
 18  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00 -30.00  146
 19  \w    -56.00   2.00   1.00   10.00    --   16.56   0.00   0.00   58
 20  \w    -56.00  90.00   1.00   10.00    --   16.56   0.00 -90.00  146
;
_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      -0.0275420000
_diffrn_orient_matrix_UB_12      0.0330820000
_diffrn_orient_matrix_UB_13      0.0185728000
_diffrn_orient_matrix_UB_21      -0.0265255000
_diffrn_orient_matrix_UB_22      -0.0259091000
_diffrn_orient_matrix_UB_23      0.0324340000
_diffrn_orient_matrix_UB_31      0.0569882000
_diffrn_orient_matrix_UB_32      0.0039238000
_diffrn_orient_matrix_UB_33      0.0576070000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.418
_diffrn_reflns_theta_min         3.145
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol-water'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.481
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.188
_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     183
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0207P)^2^+4.4459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2780
_reflns_number_total             3938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00760f2.cif
_cod_data_source_block           sqa-pica-1-1-jul
_cod_database_code               7245653
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.0903(10)
 0.9097(10)
;
_shelx_res_checksum              11487
_shelx_hkl_checksum              62633
_olex2_date_sample_data_collection 2019-12-22
_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 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.871