When Halogen Bonding Isn't Enough: Solvation Behavior in Cocrystals of Benzyltrimethylammonium Halides and 1,4-Diiodotetrafluorobenzene
Peloquin, Andrew J.; Pelendage, Lahiruni; Alapati, Srikar; Hanks, Timothy; McMillen, Colin; Pennington, William; CrystEngComm  (2025) –; doi:10.1039/D5CE00832H

data_7251423
_publ_section_title
;
 When Halogen Bonding Isn't Enough: Solvation Behavior in Cocrystals of
 Benzyltrimethylammonium Halides and 1,4-Diiodotetrafluorobenzene
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00832H
_journal_year                    2025
_chemical_formula_moiety         '4(C6 F4 I2), 3(C10 H16 N), 3(Br)'
_chemical_formula_sum            'C54 H48 Br3 F16 I8 N3'
_chemical_formula_weight         2297.924
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-29 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1473(6)
_cell_length_b                   23.2966(7)
_cell_length_c                   13.1846(4)
_cell_measurement_reflns_used    9336
_cell_measurement_temperature    99.95
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.51
_cell_volume                     6802.7(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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<i>b</i>)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      99.95
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.9980
_diffrn_reflns_Laue_measured_fraction_max 0.9953
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            81257
_diffrn_reflns_point_group_measured_fraction_full 0.9944
_diffrn_reflns_point_group_measured_fraction_max 0.9724
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.00
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.490
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             4251.542
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.287
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.7839
_refine_diff_density_min         -0.9750
_refine_diff_density_rms         0.1728
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_d_res_high            0.6989
_refine_ls_d_res_low             10.1882
_refine_ls_goodness_of_fit_ref   1.0443
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    75
_refine_ls_number_parameters     767
_refine_ls_number_reflns         20271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0443
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0128P)^2^+2.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0564
_reflns_Friedel_coverage         0.948
_reflns_limit_h_max              31
_reflns_limit_h_min              -31
_reflns_limit_k_max              33
_reflns_limit_k_min              -33
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                17930
_reflns_number_total             20271
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           3(NMe3BzBr)_4(pF4DIB)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7251423
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.767764
 0.232236
2.a Secondary CH2 refined with riding coordinates:
 C24(H24a,H24b), C4(H4a,H4b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C6(H6), C7(H7), C8(H8),
 C9(H9), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C1(H1a,H1b,
 H1c), C2(H2a,H2b,H2c), C3(H3a,H3b,H3c), C11(H11a,H11b,H11c), C12(H12a,H12b,
 H12c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'