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_7251429
_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, 2(C3 F2 I), C3 H8 O, C10 H16 N'
_chemical_formula_sum            'C19 H24 F4 I3 N O'
_chemical_formula_weight         739.115
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_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                93.193(4)
_cell_angle_beta                 98.928(4)
_cell_angle_gamma                90.425(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6413(9)
_cell_length_b                   11.6873(12)
_cell_length_c                   12.0058(13)
_cell_measurement_reflns_used    9717
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.93
_cell_volume                     1195.8(2)
_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      100.0
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9943
_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9943
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43064
_diffrn_reflns_point_group_measured_fraction_full 0.9965
_diffrn_reflns_point_group_measured_fraction_max 0.9943
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.38
_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    3.961
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0710 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8247.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.053
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             694.031
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.5030
_refine_diff_density_min         -0.5036
_refine_diff_density_rms         0.0950
_refine_ls_d_res_high            0.7086
_refine_ls_d_res_low             8.5607
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0481
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0070P)^2^+0.8553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0345
_refine_ls_wR_factor_ref         0.0366
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                6508
_reflns_number_total             6997
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           NMe3BzI_pF4DIB_iPrOH
_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               7251429
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C17(H17)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
1.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c),
 C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'