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_7251422
_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         '3(C6 F4 I2), 3(Cl), C H Cl3, 3(C10 H16 N)'
_chemical_formula_sum            'C49 H49 Cl6 F12 I6 N3'
_chemical_formula_weight         1882.078
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_Int_Tables_number      5
_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                 90.252(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.5735(16)
_cell_length_b                   13.3979(9)
_cell_length_c                   21.0751(13)
_cell_measurement_reflns_used    9153
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.62
_cell_volume                     6373.8(7)
_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      99.98
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9974
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9974
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            100705
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9925
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         1.93
_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    3.246
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4432
_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    1.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3564.083
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.197
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         2.0279
_refine_diff_density_min         -1.2083
_refine_diff_density_rms         0.1924
_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   0.008(8)
_refine_ls_d_res_high            0.6988
_refine_ls_d_res_low             10.5374
_refine_ls_goodness_of_fit_ref   1.0398
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    77
_refine_ls_number_parameters     694
_refine_ls_number_reflns         19430
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.0395
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          -0.0017
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0051P)^2^+50.7601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.987
_reflns_limit_h_max              32
_reflns_limit_h_min              -32
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              30
_reflns_limit_l_min              -30
_reflns_number_gt                17967
_reflns_number_total             19430
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           3(NMe3BzCl)_3(pF4DIB)_2(CHCl3)
_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     ' C 2y'
_cod_database_code               7251422
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C29 \\sim C28 \\sim C27: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
2.a Ternary CH refined with riding coordinates:
 C49(H49)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C14(H14a,H14b), C24(H24a,H24b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C3(H3a,H3b,H3c), C11(H11a,H11b,H11c),
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C21(H21a,H21b,H21c), C22(H22a,H22b,
 H22c), C23(H23a,H23b,H23c)
;
_olex2_submission_special_instructions 'No special instructions were received'