I⋯N halogen bonding in 1 : 1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): assessment of supramolecular association and influence upon solid-state photoluminescence properties
Yeo, Chien Ing; Tan, Yee Seng; Kwong, Huey Chong; Lee, Vannajan Sanghiran; Tiekink, Edward R. T.; CrystEngComm  (2022) –; doi:10.1039/D2CE01165D

data_7245682
_publ_section_title
;
 I&#x22EF;N halogen bonding in 1&#x2009;:&#x2009;1 co-crystals formed
 between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines
 (n = 2, 3 and 4): assessment of supramolecular association and influence
 upon solid-state photoluminescence properties
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01165D
_journal_year                    2022
_chemical_formula_moiety         'C12 H10 N4, C6 F4 I2'
_chemical_formula_sum            'C18 H10 F4 I2 N4'
_chemical_formula_weight         612.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-20 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1887(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.5350(4)
_cell_length_b                   4.12409(7)
_cell_length_c                   38.7414(6)
_cell_measurement_reflns_used    14545
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2360
_cell_measurement_theta_min      3.7440
_cell_volume                     3744.95(11)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            23058
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.290
_diffrn_reflns_theta_min         3.772
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    26.854
_exptl_absorpt_correction_T_max  0.320
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.171
_exptl_crystal_description       prism
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.919
_refine_diff_density_min         -2.294
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+7.2152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0901
_refine_special_details
;
The maximum and minimum residual electron density peaks of 0.92 and 2.29
e/ang3 are located 1.08 and 0.70 ang from the I2 and I1 atoms, respectively.

Owing to poor agreement, two reflections, i.e. (1 5 10) and (-1 5 6), were
omitted from the final cycles of refinement.
;
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3811
_reflns_number_total             3857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01165d2.cif
_cod_data_source_block           shelx_CCDC2
_cod_original_cell_volume        3744.95(10)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7245682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.043
_shelx_estimated_absorpt_t_max   0.664
_shelx_res_checksum              94635
_shelx_hkl_checksum              70213