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_7251425
_publ_section_title
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 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(I), 4(C6 F4 I2), 4(C10 H16 N), C2 H3 N'
_chemical_formula_sum            'C66 H67 F16 I12 N5'
_chemical_formula_weight         2757.129
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_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                 121.183(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   26.8437(10)
_cell_length_b                   7.2678(3)
_cell_length_c                   25.9199(14)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      3.04
_cell_volume                     4326.2(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 0.9959
_diffrn_measured_fraction_theta_max 0.9968
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.9959
_diffrn_reflns_Laue_measured_fraction_max 0.9968
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            44675
_diffrn_reflns_point_group_measured_fraction_full 0.9959
_diffrn_reflns_point_group_measured_fraction_max 0.9968
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.94
_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    4.368
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0824 before and 0.0425 after correction.
The Ratio of minimum to maximum transmission is 0.7914.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2547.975
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.176
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.7335
_refine_diff_density_min         -1.3603
_refine_diff_density_rms         0.1276
_refine_ls_d_res_high            0.7697
_refine_ls_d_res_low             6.9291
_refine_ls_goodness_of_fit_ref   1.0521
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.0498
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+22.3072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0557
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              29
_reflns_limit_h_min              -34
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                4569
_reflns_number_total             4959
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           4(NMe3BzI)_4(pF4DIB)_MeCN
_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               7251425
_olex2_refinement_description
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1. Restrained distances
 N17-C18
 1.15 with sigma of 0.02
 C18-C19
 1.5 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(N17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
3. Others
 Fixed Sof: N17(0.25) C18(0.25) C19(0.25) H19a(0.25) H19b(0.25) H19c(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b)
4.b Me refined with riding coordinates:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
4.d Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'