Hierarchy and cooperativity between π-type halogen bonds and aromatic carboxylic acid dimers in co-crystal formation
Feld, Emmett H.; Bosch, Eric; Unruh, Daniel K.; Krueger, Herman R.; Groeneman, Ryan H.; CrystEngComm 27 (2025) 5100–5103; doi:10.1039/D5CE00551E

data_7250657
_publ_section_title
;
 Hierarchy and cooperativity between \p-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(C9 H8 O2)'
_chemical_formula_sum            'C24 H16 Cl4 I2 O4'
_chemical_formula_weight         763.97
_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
_audit_creation_date             2025-05-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-19 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                87.260(2)
_cell_angle_beta                 82.1720(10)
_cell_angle_gamma                82.178(2)
_cell_formula_units_Z            1
_cell_length_a                   5.3023(2)
_cell_length_b                   6.6859(3)
_cell_length_c                   18.7003(9)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      28.308
_cell_measurement_theta_min      2.200
_cell_volume                     650.36(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.990
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24563
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.465
_diffrn_reflns_theta_min         2.200
_exptl_absorpt_coefficient_mu    2.858
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0648 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.7730.
The \l/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    1.951
_exptl_crystal_description       plate
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0222
_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/[\s^2^(Fo^2^)+(0.0089P)^2^+0.6165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             3246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00551e2.cif
_cod_data_source_block           C6I2Cl4_2cinn
_cod_depositor_comments
'Adding full bibliography for 7250656--7250657.cif.'
_cod_database_code               7250657
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.603
_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), C10(H10), C11(H11)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              94765
_olex2_submission_special_instructions 'No special instructions were received'