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_2312434
_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         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1094(2)
_cell_length_b                   5.9629(2)
_cell_length_c                   29.6773(8)
_cell_measurement_reflns_used    3954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.8770
_cell_measurement_theta_min      2.9790
_cell_volume                     1258.10(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_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    -24.00  22.00   0.50    0.20    --  -47.13  24.00-110.00   92
  2  \w    -47.00 -21.00   0.50    0.20    --  -47.13 128.00 105.00   52
  3  \w    -95.00 -69.00   0.50    0.20    --  -47.13 128.00 105.00   52
  4  \w   -177.00-134.00   0.50    1.00    -- -106.00-100.00 -75.00   86
  5  \w     72.00 178.00   0.50    1.00    --  113.25 128.00 105.00  212
  6  \w    -16.00  23.00   0.50    0.20    --  -47.13  19.00  30.00   78
  7  \w    -21.00  22.00   0.50    0.20    --  -47.13  19.00 -60.00   86
  8  \w    -68.00 -41.00   0.50    1.00    -- -106.00  61.00 -30.00   54
  9  \w   -164.00 -95.00   0.50    1.00    -- -106.00 -24.00  84.00  138
 10  \w    -71.00 -45.00   0.50    1.00    -- -106.00  61.00-150.00   52
 11  \w     45.00  71.00   0.50    1.00    --  113.25 -61.00  90.00   52
 12  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00 150.00   50
 13  \w     72.00  97.00   0.50    1.00    --  113.25-100.00 -75.00   50
 14  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00  60.00   50
 15  \w     47.00  82.00   0.50    1.00    --  113.25 -77.00-150.00   70
 16  \w   -103.00 -77.00   0.50    0.20    --  -47.13-128.00  30.00   52
 17  \w    -93.00 -50.00   0.50    0.20    --  -47.13 125.00-180.00   86
 18  \w     27.00  52.00   0.50    0.20    --   47.13 -57.00 -90.00   50
 19  \w    -16.00  12.00   0.50    0.20    --   47.13 -19.00  30.00   56
 20  \w    -24.00   1.00   0.50    0.20    --   47.13 -57.00 -90.00   50
 21  \w    -18.00  23.00   0.50    0.20    --   47.13 -19.00   0.00   82
 22  \w     79.00 115.00   0.50    0.20    --   47.13 128.00 105.00   72
 23  \w    -13.00  26.00   0.50    0.20    --   47.13 -19.00  60.00   78
 24  \w   -164.00-105.00   0.50    1.00    -- -106.00 -45.00-120.00  118
 25  \w   -171.00-158.50   0.50    1.00    -- -106.00 -15.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0838686000
_diffrn_orient_matrix_UB_12      0.0777902000
_diffrn_orient_matrix_UB_13      -0.0452465000
_diffrn_orient_matrix_UB_21      -0.1994837000
_diffrn_orient_matrix_UB_22      -0.0188453000
_diffrn_orient_matrix_UB_23      0.0199165000
_diffrn_orient_matrix_UB_31      0.0112213000
_diffrn_orient_matrix_UB_32      0.2455551000
_diffrn_orient_matrix_UB_33      0.0158985000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6315
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.992
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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    1.427
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0523P)^2^+0.4708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1049
_reflns_number_total             1175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5083sup1.cif
_cod_data_source_block           4
_cod_database_code               2312434
_chemical_oxdiff_formula         'C16 H14 O4'
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.786
_cod_database_fobs_code 2312434