#------------------------------------------------------------------------------
#$Date: 2024-03-23 05:02:06 +0200 (Sat, 23 Mar 2024) $
#$Revision: 290606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312432.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_2312432
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         'C22 H16 I2 O4'
_chemical_formula_sum            'C22 H16 I2 O4'
_chemical_formula_weight         598.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.084(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4580(3)
_cell_length_b                   14.6955(5)
_cell_length_c                   9.7079(4)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2820
_cell_measurement_theta_min      4.2570
_cell_volume                     992.75(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -99.00 -72.00   1.00   20.00    --  -16.78-178.00-150.00   27
  2  ω     -7.00  75.00   1.00   20.00    --   18.97  57.00  90.00   82
  3  ω     -9.00  97.00   1.00   20.00    --   18.97  19.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0760731000
_diffrn_orient_matrix_UB_12      -0.0320980000
_diffrn_orient_matrix_UB_13      -0.0184316000
_diffrn_orient_matrix_UB_21      -0.0362074000
_diffrn_orient_matrix_UB_22      0.0170154000
_diffrn_orient_matrix_UB_23      -0.0732620000
_diffrn_orient_matrix_UB_31      0.0573607000
_diffrn_orient_matrix_UB_32      -0.0317595000
_diffrn_orient_matrix_UB_33      -0.0206688000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5135
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (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    2.001
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.911
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0242
_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)+(0.0261P)²+2.5099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             2282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5083sup1.cif
_cod_data_source_block           2
_cod_database_code               2312432
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H16 O4 I2'
_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   0.597
_shelx_estimated_absorpt_t_min   0.468
_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), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.734
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
I1 I 0.78106(3) 0.53813(2) 0.12200(2) 0.01672(9) Uani 1 1 d . . . . .
O1 O 0.1948(3) 0.87799(14) 0.3065(2) 0.0190(4) Uani 1 1 d . . . . .
O2 O 0.0125(3) 0.75271(15) 0.2430(3) 0.0211(5) Uani 1 1 d . . . . .
C1 C 0.3474(4) 0.7331(2) 0.3330(3) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.5293(4) 0.7671(2) 0.4120(3) 0.0159(5) Uani 1 1 d . . . . .
H2 H 0.544992 0.829369 0.440387 0.019 Uiso 1 1 calc R U . . .
C3 C 0.6879(4) 0.7102(2) 0.4494(3) 0.0152(5) Uani 1 1 d . . . . .
H3 H 0.811955 0.733370 0.504538 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6663(4) 0.6188(2) 0.4063(3) 0.0134(5) Uani 1 1 d . . . . .
C5 C 0.4834(4) 0.5851(2) 0.3268(3) 0.0165(6) Uani 1 1 d . . . . .
H5 H 0.467621 0.523122 0.296896 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3248(4) 0.6416(2) 0.2912(3) 0.0168(6) Uani 1 1 d . . . . .
H6 H 0.200286 0.618079 0.238335 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8377(4) 0.55792(19) 0.4507(3) 0.0133(5) Uani 1 1 d . . . . .
C8 C 0.9051(4) 0.51537(19) 0.3503(3) 0.0132(5) Uani 1 1 d . . . . .
C9 C 1.0645(4) 0.45816(19) 0.3991(3) 0.0140(5) Uani 1 1 d . . . . .
H9 H 1.107452 0.429517 0.328847 0.017 Uiso 1 1 calc R U . . .
C10 C 0.1804(4) 0.7964(2) 0.2944(3) 0.0158(6) Uani 1 1 d . . . . .
C11 C -0.1552(5) 0.8113(2) 0.1916(4) 0.0269(7) Uani 1 1 d . . . . .
H11A H -0.146903 0.850977 0.112987 0.040 Uiso 1 1 calc R U . . .
H11B H -0.160371 0.848577 0.273790 0.040 Uiso 1 1 calc R U . . .
H11C H -0.271445 0.773897 0.153339 0.040 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 0.0033 0.0016 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C10 O2 C11 114.8(2) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C10 118.4(3) . . ?
C6 C1 C10 121.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 119.7(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 C7 120.8(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C4 123.7(3) . . ?
C8 C7 C9 118.0(3) . 3_766 ?
C9 C7 C4 118.3(3) 3_766 . ?
C7 C8 I1 122.2(2) . . ?
C9 C8 I1 117.0(2) . . ?
C9 C8 C7 120.7(3) . . ?
C7 C9 H9 119.4 3_766 . ?
C8 C9 C7 121.3(3) . 3_766 ?
C8 C9 H9 119.4 . . ?
O1 C10 O2 123.6(3) . . ?
O1 C10 C1 124.0(3) . . ?
O2 C10 C1 112.3(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
I1 C8 2.099(3) . ?
O1 C10 1.205(4) . ?
O2 C10 1.334(4) . ?
O2 C11 1.451(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.397(4) . ?
C1 C10 1.491(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.492(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(4) . ?
C7 C9 1.396(4) 3_766 ?
C8 C9 1.392(4) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
I1 C8 C9 C7 177.1(2) . . . 3_766 ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C10 O1 12.2(5) . . . . ?
C2 C1 C10 O2 -168.6(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C7 -178.5(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C7 C8 -117.4(3) . . . . ?
C3 C4 C7 C9 63.1(4) . . . 3_766 ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C7 C8 I1 3.6(4) . . . . ?
C4 C7 C8 C9 -179.0(3) . . . . ?
C5 C4 C7 C8 64.8(4) . . . . ?
C5 C4 C7 C9 -114.6(3) . . . 3_766 ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C1 C10 O1 -167.6(3) . . . . ?
C6 C1 C10 O2 11.7(4) . . . . ?
C7 C4 C5 C6 177.6(3) . . . . ?
C7 C8 C9 C7 -0.4(5) . . . 3_766 ?
C9 C7 C8 I1 -176.9(2) 3_766 . . . ?
C9 C7 C8 C9 0.4(4) 3_766 . . . ?
C10 C1 C2 C3 -179.8(3) . . . . ?
C10 C1 C6 C5 178.9(3) . . . . ?
C11 O2 C10 O1 4.4(4) . . . . ?
C11 O2 C10 C1 -174.9(3) . . . . ?

_cod_database_fobs_code 2312432
