Effect of a halogen bond on the crystal structure of terphenyldicarboxylic acid derivatives.
Osipov, Artyom A.; Nayfert, Sergey A.; Sobalev, Sergey A.; Rajakumar, Kanthapazham; Zherebtsov, Dmitry A.; Spiridonova, Dar'ya V.; Vinnik, Denis A.; Acta crystallographica Section B, Structural science, crystal engineering and materials 80 (2024) –; doi:10.1107/S2052520624001318

data_2312433
_publ_section_title
;
 Effect of a halogen bond on the crystal structure of
 terphenyldicarboxylic acid derivatives.
;
_journal_coeditor_code           AW5083
_journal_issue                   2
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_paper_doi               10.1107/S2052520624001318
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 K O4'
_chemical_formula_sum            'C20 H13 K O4'
_chemical_formula_weight         356.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.359(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.01260(10)
_cell_length_b                   6.9783(2)
_cell_length_c                   34.9410(7)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9750
_cell_measurement_theta_min      2.5110
_cell_volume                     1463.53(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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    -82.00 -56.00   0.50    7.50    --  -35.49 141.00 -19.00   52
  2  \w    -86.00 -22.00   0.50    7.50    --  -35.49 129.00 168.00  128
  3  \w     27.00  52.00   0.50    7.50    --   35.49-129.00  94.00   50
  4  \w     15.00  40.00   0.50    7.50    --   35.49-141.00 -77.00   50
  5  \w     92.00 117.00   0.50   30.00    --  100.00 129.00 168.00   50
  6  \w    109.00 134.00   0.50   30.00    --  100.00 141.00 -19.00   50
  7  \w     65.00  91.00   0.50   30.00    --  100.00-129.00  94.00   52
  8  \w     99.00 124.00   0.50   30.00    --  100.00-141.00 -77.00   50
  9  \w    -64.00 -16.00   0.50    7.50    --  -35.49  21.00 -30.00   96
 10  \w   -101.00 -76.00   0.50    7.50    --  -35.49 -54.00-120.00   50
 11  \w     -8.00  35.00   0.50    7.50    --  -35.49  77.00  30.00   86
 12  \w     10.00  40.00   0.50    7.50    --  -35.49  21.00 -30.00   60
 13  \w    -67.00 -35.00   0.50    7.50    --  -35.49 -54.00-120.00   64
 14  \w    -63.00 -37.00   0.50    7.50    --  -35.49  77.00  30.00   52
 15  \w    -10.00  16.00   0.50    7.50    --   35.49 -65.00  90.00   52
 16  \w    -29.00  20.00   0.50    7.50    --   35.49 -89.00 120.00   98
 17  \w     28.00  68.00   0.50    7.50    --   35.49 -89.00 120.00   80
 18  \w     27.00 105.00   0.50    7.50    --   35.49  43.00-180.00  156
 19  \w     36.00  61.00   0.50    7.50    --   35.49 -65.00  90.00   50
 20  \w     -9.00  47.00   0.50    7.50    --   35.49-104.00  60.00  112
 21  \w    -11.00  15.00   0.50    7.50    --   35.49 -32.00 -60.00   52
 22  \w    102.00 127.00   0.50   30.00    --  100.00 -69.00  30.00   50
 23  \w     62.00 111.00   0.50   30.00    --  100.00-125.00 -90.00   98
 24  \w     33.00  88.00   0.50   30.00    --  100.00 -69.00  90.00  110
 25  \w     98.00 124.00   0.50   30.00    --  100.00  69.00   0.00   52
 26  \w     26.00 107.00   0.50   30.00    --  100.00-107.00  90.00  162
 27  \w     89.00 157.00   0.50   30.00    --  100.00 107.00-150.00  136
 28  \w     90.00 146.00   0.50   30.00    --  100.00  91.00 -90.00  112
 29  \w     90.00 144.00   0.50   30.00    --  100.00 107.00 -60.00  108
 30  \w     83.00 157.00   0.50   30.00    --  100.00  77.00-120.00  148
 31  \w     68.00 133.00   0.50   30.00    --  100.00 -86.00  90.00  130
 32  \w    125.00 156.00   0.50   30.00    --  100.00  69.00   0.00   62
 33  \w     82.00 153.00   0.50   30.00    --  100.00  61.00  30.00  142
 34  \w     34.00 117.00   0.50   30.00    --  100.00 -45.00  90.00  166
 35  \w     76.00 101.00   0.50   30.00    --  100.00  69.00 150.00   50
 36  \w     36.00  64.00   0.50   30.00    --  100.00 -69.00  30.00   56
 37  \w     61.00 104.00   0.50   30.00    --  100.00-107.00  30.00   86
 38  \w     74.00 100.00   0.50   30.00    --  100.00-107.00 -60.00   52
 39  \w     97.00 127.00   0.50   30.00    --  100.00 -69.00  90.00   60
 40  \w     50.00  76.00   0.50   30.00    --  100.00-125.00   0.00   52
 41  \w    120.00 145.00   0.50   30.00    --  100.00  91.00 -60.00   50
 42  \w     87.00 118.00   0.50   30.00    --  100.00  91.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1297811000
_diffrn_orient_matrix_UB_12      0.1460793000
_diffrn_orient_matrix_UB_13      -0.0230944000
_diffrn_orient_matrix_UB_21      0.1038392000
_diffrn_orient_matrix_UB_22      -0.1652131000
_diffrn_orient_matrix_UB_23      -0.0221313000
_diffrn_orient_matrix_UB_31      -0.1956670000
_diffrn_orient_matrix_UB_32      0.0091164000
_diffrn_orient_matrix_UB_33      -0.0304500000
_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  0.0095
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            3516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.105
_diffrn_reflns_theta_min         2.533
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0518P)^2^+1.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1331
_reflns_number_total             1366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5083sup1.cif
_cod_data_source_block           3
_cod_database_code               2312433
_chemical_oxdiff_formula         'C20 H13 O4 K'
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
;
_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.827
_cod_database_fobs_code 2312433