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#$Date: 2025-08-06 00:36:03 +0300 (Wed, 06 Aug 2025) $
#$Revision: 301572 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/06/7250656.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7250656
loop_
_publ_author_name
'Feld, Emmett H.'
'Bosch, Eric'
'Unruh, Daniel K.'
'Krueger, Herman R.'
'Groeneman, Ryan H.'
_publ_section_title
;
 Hierarchy and cooperativity between π-type halogen bonds and aromatic
 carboxylic acid dimers in co-crystal formation
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5100
_journal_page_last               5103
_journal_paper_doi               10.1039/D5CE00551E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C6 Cl4 I2, 2(C7 H6 O2)'
_chemical_formula_sum            'C20 H12 Cl4 I2 O4'
_chemical_formula_weight         711.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-05-19 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                99.824(2)
_cell_angle_beta                 94.165(2)
_cell_angle_gamma                99.031(2)
_cell_formula_units_Z            1
_cell_length_a                   5.4271(3)
_cell_length_b                   6.5120(4)
_cell_length_c                   16.5542(10)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      27.783
_cell_measurement_theta_min      2.509
_cell_volume                     566.34(6)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS Inc, 2024)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS Inc, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture DUO with Photon 3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         2.510
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.274
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.8377.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_description       plate
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0142P)²+0.3036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2550
_reflns_number_total             2832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00551e2.cif
_cod_data_source_block           C6I2Cl4_2benz
_cod_depositor_comments
'Adding full bibliography for 7250656--7250657.cif.'
_cod_database_code               7250656
_shelx_shelxl_version_number     2019/3
_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   0.777
_shelx_estimated_absorpt_t_min   0.516
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5) H2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I1 I 0.16998(3) 0.77539(2) 0.14338(2) 0.04837(7) Uani 1 1 d . . . . .
Cl1 Cl 0.50786(13) 0.40707(11) 0.17797(4) 0.05480(15) Uani 1 1 d . . . . .
Cl2 Cl 0.80199(12) 0.16707(9) 0.05312(4) 0.05192(15) Uani 1 1 d . . . . .
C1 C 0.3666(4) 0.6102(3) 0.05766(13) 0.0341(4) Uani 1 1 d . . . . .
C2 C 0.5009(4) 0.4590(3) 0.07946(13) 0.0355(4) Uani 1 1 d . . . . .
C3 C 0.6341(4) 0.3500(3) 0.02263(13) 0.0347(4) Uani 1 1 d . . . . .
O1 O -0.1827(4) 0.5827(3) 0.42707(13) 0.0615(5) Uani 1 1 d . . . . .
H1 H -0.163570 0.493605 0.455405 0.092 Uiso 0.5 1 calc R U P . .
O2 O 0.2089(4) 0.7137(3) 0.48265(13) 0.0630(5) Uani 1 1 d . . . . .
H2 H 0.181639 0.613553 0.506697 0.094 Uiso 0.5 1 calc R U P . .
C4 C 0.0267(4) 0.8887(4) 0.38616(14) 0.0431(5) Uani 1 1 d . . . . .
C5 C -0.1763(5) 0.8939(4) 0.33038(15) 0.0493(5) Uani 1 1 d . . . . .
H5 H -0.316959 0.788131 0.323088 0.059 Uiso 1 1 calc R U . . .
C6 C -0.1693(5) 1.0547(5) 0.28609(17) 0.0548(6) Uani 1 1 d . . . . .
H6 H -0.304436 1.056621 0.248499 0.066 Uiso 1 1 calc R U . . .
C7 C 0.0378(5) 1.2132(5) 0.29726(17) 0.0549(6) Uani 1 1 d . . . . .
H7 H 0.041105 1.322573 0.267635 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2392(5) 1.2097(5) 0.35211(17) 0.0575(6) Uani 1 1 d . . . . .
H8 H 0.378485 1.316764 0.359423 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2354(5) 1.0481(4) 0.39631(15) 0.0506(6) Uani 1 1 d . . . . .
H9 H 0.372730 1.045749 0.432960 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0162(4) 0.7166(4) 0.43481(15) 0.0470(5) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C2 C1 I1 120.74(15) . . ?
C2 C1 C3 118.80(18) . 2_665 ?
C3 C1 I1 120.46(14) 2_665 . ?
C1 C2 Cl1 120.10(16) . . ?
C1 C2 C3 120.87(19) . . ?
C3 C2 Cl1 119.03(16) . . ?
C1 C3 Cl2 120.54(16) 2_665 . ?
C2 C3 Cl2 119.13(16) . . ?
C2 C3 C1 120.33(18) . 2_665 ?
C10 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C5 C4 C10 120.0(2) . . ?
C9 C4 C5 119.1(2) . . ?
C9 C4 C10 120.9(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
O1 C10 O2 123.6(2) . . ?
O1 C10 C4 118.6(2) . . ?
O2 C10 C4 117.8(2) . . ?
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 C1 2.090(2) . ?
Cl1 C2 1.720(2) . ?
Cl2 C3 1.727(2) . ?
C1 C2 1.392(3) . ?
C1 C3 1.397(3) 2_665 ?
C2 C3 1.394(3) . ?
O1 H1 0.8200 . ?
O1 C10 1.260(3) . ?
O2 H2 0.8200 . ?
O2 C10 1.270(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.390(3) . ?
C4 C10 1.484(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.83 2.629(3) 165.2 2_566 yes
O2 H2 O1 0.82 1.82 2.629(3) 168.0 2_566 yes
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 C1 C2 Cl1 -0.3(2) . . . . ?
I1 C1 C2 C3 -179.42(15) . . . . ?
Cl1 C2 C3 Cl2 -0.2(2) . . . . ?
Cl1 C2 C3 C1 -179.57(15) . . . 2_665 ?
C1 C2 C3 Cl2 178.94(16) . . . . ?
C1 C2 C3 C1 -0.5(3) . . . 2_665 ?
C3 C1 C2 Cl1 179.55(15) 2_665 . . . ?
C3 C1 C2 C3 0.5(3) 2_665 . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C4 C9 C8 0.6(4) . . . . ?
C5 C4 C10 O1 -3.1(3) . . . . ?
C5 C4 C10 O2 177.4(2) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C9 C4 C5 C6 0.0(4) . . . . ?
C9 C4 C10 O1 175.8(2) . . . . ?
C9 C4 C10 O2 -3.6(3) . . . . ?
C10 C4 C5 C6 179.0(2) . . . . ?
C10 C4 C9 C8 -178.3(2) . . . . ?
