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_7251419
_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         '2(C6 F4 I2), 2(Cl), 2(C10 H16 N), C2 H3 N'
_chemical_formula_sum            'C34 H35 Cl2 F8 I4 N3'
_chemical_formula_weight         1216.187
_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
;
2025-07-29 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.023(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.683(2)
_cell_length_b                   7.3274(5)
_cell_length_c                   24.0892(19)
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.92
_cell_volume                     4001.8(5)
_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      99.99
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9919
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.9947
_diffrn_reflns_Laue_measured_fraction_max 0.9919
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            38801
_diffrn_reflns_point_group_measured_fraction_full 0.9947
_diffrn_reflns_point_group_measured_fraction_max 0.9919
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.92
_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    3.314
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6100
_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    2.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2308.237
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.331
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.3337
_refine_diff_density_min         -1.0132
_refine_diff_density_rms         0.2179
_refine_ls_d_res_high            0.6988
_refine_ls_d_res_low             6.9723
_refine_ls_goodness_of_fit_ref   1.0654
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.0620
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+49.4797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              -36
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                5492
_reflns_number_total             6097
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00832h2.cif
_cod_data_source_block           2(NMe3BzCl)_2(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_original_cell_volume        4001.9(5)
_cod_database_code               7251419
_olex2_refinement_description
;
1. Restrained distances
 N3-C17
 1.14 with sigma of 0.02
 C18-N3
 2.593 with sigma of 0.02
 C17-N3
 1.137 with sigma of 0.01
 C17-C18
 1.456 with sigma of 0.01
 N3-C18
 2.59 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
N3 \\sim C17 \\sim C18: within 2A with sigma of 0.05 and sigma for terminal
atoms of 0.01 within 2A
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 N3, C17, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: N3(0.5) C17(0.5) C18(0.5) H18a(0.5) H18b(0.5) H18c(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
5.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C3(H3a,H3b,H3c), C18(H18a,H18b,H18c)
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_olex2_submission_special_instructions 'No special instructions were received'