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_7251426
_publ_section_title
;
 When Halogen Bonding Isn't Enough: Solvation Behavior in Cocrystals of
 Benzyltrimethylammonium Halides and 1,4-Diiodotetrafluorobenzene
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_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00832H
_journal_year                    2025
_chemical_formula_moiety         '4(I), 4(C6 F4 I2), 3(C3 H6 O), 4(C10 H16 N)'
_chemical_formula_sum            'C73 H82 F16 I12 N4 O3'
_chemical_formula_weight         2890.318
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_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
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2025-07-30 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.270(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.9831(9)
_cell_length_b                   13.9458(10)
_cell_length_c                   22.4748(14)
_cell_measurement_reflns_used    9082
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.68
_cell_volume                     4695.0(5)
_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      150.17
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9963
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9963
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            88511
_diffrn_reflns_point_group_measured_fraction_full 0.9967
_diffrn_reflns_point_group_measured_fraction_max 0.9958
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.89
_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    4.032
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1143 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.6752.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             2696.079
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.1805
_refine_diff_density_min         -0.9560
_refine_diff_density_rms         0.1598
_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(7)
_refine_ls_d_res_high            0.7483
_refine_ls_d_res_low             7.0586
_refine_ls_goodness_of_fit_ref   1.0400
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    124
_refine_ls_number_parameters     973
_refine_ls_number_reflns         23365
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.0396
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          -0.0021
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0176P)^2^+5.5717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0583
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              29
_reflns_limit_l_min              -29
_reflns_number_gt                20599
_reflns_number_total             23365
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           4(NMe3BzI)_4(pF4DIB)_3(acetone)
_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 2yb'
_cod_database_code               7251426
_olex2_refinement_description
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1. Uiso/Uaniso restraints and constraints
C66 \\sim C67: within 4A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 4A
C28 \\sim C29 \\sim C30: within 4A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 4A
O3 \\sim C71 \\sim C73 \\sim C72: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
2.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C11(H11a,H11b), C21(H21a,H21b), C31(H31a,H31b)
2.b Me refined with riding coordinates:
 C66(H66a,H66b,H66c), C67(H67a,H67b,H67c), C69(H69a,H69b,H69c), C70(H70a,H70b,
 H70c), C72(H72a,H72b,H72c), C73(H73a,H73b,H73c), C8(H8a,H8b,H8c), C9(H9a,H9b,
 H9c), C10(H10a,H10b,H10c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C20(H20a,
 H20b,H20c), C28(H28a,H28b,H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c),
 C38(H38a,H38b,H38c), C39(H39a,H39b,H39c), C40(H40a,H40b,H40c)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C33(H33),
  C34(H34), C35(H35), C36(H36), C37(H37)
;
_olex2_submission_special_instructions 'No special instructions were received'