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_7251414
_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         'I, C6 F4 I2, C2 H6 O, C10 H16 N'
_chemical_formula_sum            'C18 H22 F4 I3 N O'
_chemical_formula_weight         725.088
_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'
_symmetry_Int_Tables_number      61
_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
;
2025-07-30 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            8
_cell_length_a                   23.0021(8)
_cell_length_b                   8.6231(3)
_cell_length_c                   23.1475(8)
_cell_measurement_reflns_used    9132
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.95
_cell_volume                     4591.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX3'
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9976
_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  0.0745
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.9974
_diffrn_reflns_Laue_measured_fraction_max 0.9976
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41634
_diffrn_reflns_point_group_measured_fraction_full 0.9974
_diffrn_reflns_point_group_measured_fraction_max 0.9976
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6269
_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    2.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             2712.095
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.0901
_refine_diff_density_min         -1.2299
_refine_diff_density_rms         0.2766
_refine_ls_d_res_high            0.8108
_refine_ls_d_res_low             6.6221
_refine_ls_goodness_of_fit_ref   1.0309
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.0294
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0120P)^2^+10.0653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              28
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                3355
_reflns_number_total             4512
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           NMe3BzI_pF4DIB_EtOH
_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_database_code               7251414
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C17A \\sim C17B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C18A \\sim C18B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
2. Others
 Fixed Sof: C17A(0.5) H17a(0.5) H17b(0.5) C17B(0.5) H17c(0.5) H17d(0.5)
 C18A(0.5) H18a(0.5) H18b(0.5) H18c(0.5) C18B(0.5) H18d(0.5) H18e(0.5) H18f(0.5)
3.a Riding coordinates:
 O1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C17A(H17a,H17b), C17B(H17c,H17d), C1(H1a,H1b)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
3.d Idealised Me refined as rotating group:
 C18A(H18a,H18b,H18c), C18B(H18d,H18e,H18f), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c),
 C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'