#------------------------------------------------------------------------------
#$Date: 2024-03-23 05:02:06 +0200 (Sat, 23 Mar 2024) $
#$Revision: 290606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312434.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312434
loop_
_publ_author_name
'Osipov, Artyom A.'
'Nayfert, Sergey A.'
'Sobalev, Sergey A.'
'Rajakumar, Kanthapazham'
'Zherebtsov, Dmitry A.'
'Spiridonova, Dar'ya V.'
'Vinnik, Denis A.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -24.00  22.00   0.50    0.20    --  -47.13  24.00-110.00   92
  2  ω    -47.00 -21.00   0.50    0.20    --  -47.13 128.00 105.00   52
  3  ω    -95.00 -69.00   0.50    0.20    --  -47.13 128.00 105.00   52
  4  ω   -177.00-134.00   0.50    1.00    -- -106.00-100.00 -75.00   86
  5  ω     72.00 178.00   0.50    1.00    --  113.25 128.00 105.00  212
  6  ω    -16.00  23.00   0.50    0.20    --  -47.13  19.00  30.00   78
  7  ω    -21.00  22.00   0.50    0.20    --  -47.13  19.00 -60.00   86
  8  ω    -68.00 -41.00   0.50    1.00    -- -106.00  61.00 -30.00   54
  9  ω   -164.00 -95.00   0.50    1.00    -- -106.00 -24.00  84.00  138
 10  ω    -71.00 -45.00   0.50    1.00    -- -106.00  61.00-150.00   52
 11  ω     45.00  71.00   0.50    1.00    --  113.25 -61.00  90.00   52
 12  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00 150.00   50
 13  ω     72.00  97.00   0.50    1.00    --  113.25-100.00 -75.00   50
 14  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00  60.00   50
 15  ω     47.00  82.00   0.50    1.00    --  113.25 -77.00-150.00   70
 16  ω   -103.00 -77.00   0.50    0.20    --  -47.13-128.00  30.00   52
 17  ω    -93.00 -50.00   0.50    0.20    --  -47.13 125.00-180.00   86
 18  ω     27.00  52.00   0.50    0.20    --   47.13 -57.00 -90.00   50
 19  ω    -16.00  12.00   0.50    0.20    --   47.13 -19.00  30.00   56
 20  ω    -24.00   1.00   0.50    0.20    --   47.13 -57.00 -90.00   50
 21  ω    -18.00  23.00   0.50    0.20    --   47.13 -19.00   0.00   82
 22  ω     79.00 115.00   0.50    0.20    --   47.13 128.00 105.00   72
 23  ω    -13.00  26.00   0.50    0.20    --   47.13 -19.00  60.00   78
 24  ω   -164.00-105.00   0.50    1.00    -- -106.00 -45.00-120.00  118
 25  ω   -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       'ω 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/[σ²(Fo²)+(0.0523P)²+0.4708P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            aw5083sup1.cif
_cod_data_source_block           4
_cod_database_code               2312434
_chemical_oxdiff_formula         'C16 H14 O4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56210(12) 0.51698(14) 0.33793(3) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.44337(13) 0.19867(15) 0.30917(3) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.50609(15) 0.2190(2) 0.38798(4) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.58016(15) 0.3431(2) 0.42369(4) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.632592 0.487130 0.418254 0.022 Uiso 1 1 calc R U . . .
C3 C 0.57747(15) 0.2570(2) 0.46701(4) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.629102 0.343418 0.490895 0.021 Uiso 1 1 calc R U . . .
C4 C 0.50065(15) 0.04589(19) 0.47658(4) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.42659(15) -0.07655(19) 0.44026(4) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.372938 -0.220013 0.445611 0.022 Uiso 1 1 calc R U . . .
C6 C 0.43027(15) 0.0079(2) 0.39674(4) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.380674 -0.078939 0.372677 0.023 Uiso 1 1 calc R U . . .
C7 C 0.50040(16) 0.3056(2) 0.34097(4) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.55047(18) 0.6156(2) 0.29324(4) 0.0262(3) Uani 1 1 d . . . . .
H8A H 0.633992 0.534248 0.272680 0.039 Uiso 1 1 calc R U . . .
H8B H 0.588825 0.773327 0.294663 0.039 Uiso 1 1 calc R U . . .
H8C H 0.420752 0.605834 0.282246 0.039 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 115.11(9) . . ?
C2 C1 C7 122.57(11) . . ?
C6 C1 C2 118.88(11) . . ?
C6 C1 C7 118.53(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.22(11) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.78(11) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C4 121.33(13) . 5_656 ?
C3 C4 C5 117.23(11) . . ?
C5 C4 C4 121.43(13) . 5_656 ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.27(11) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.61(11) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C1 112.41(10) . . ?
O2 C7 O1 123.65(11) . . ?
O2 C7 C1 123.93(11) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.3378(15) . ?
O1 C8 1.4531(15) . ?
O2 C7 1.2089(15) . ?
C1 C2 1.3958(17) . ?
C1 C6 1.3940(17) . ?
C1 C7 1.4881(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3844(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.4015(16) . ?
C4 C4 1.494(2) 5_656 ?
C4 C5 1.4043(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3864(17) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.34(17) . . . . ?
C2 C1 C6 C5 0.69(16) . . . . ?
C2 C1 C7 O1 -4.03(16) . . . . ?
C2 C1 C7 O2 177.21(11) . . . . ?
C2 C3 C4 C4 179.69(12) . . . 5_656 ?
C2 C3 C4 C5 0.27(16) . . . . ?
C3 C4 C5 C6 0.28(16) . . . . ?
C4 C4 C5 C6 -179.14(12) 5_656 . . . ?
C4 C5 C6 C1 -0.77(17) . . . . ?
C6 C1 C2 C3 -0.15(16) . . . . ?
C6 C1 C7 O1 174.40(9) . . . . ?
C6 C1 C7 O2 -4.36(18) . . . . ?
C7 C1 C2 C3 178.28(10) . . . . ?
C7 C1 C6 C5 -177.80(10) . . . . ?
C8 O1 C7 O2 1.98(16) . . . . ?
C8 O1 C7 C1 -176.78(9) . . . . ?

_cod_database_fobs_code 2312434
