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_7245680
_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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 91.4133(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.19820(11)
_cell_length_b                   9.94832(12)
_cell_length_c                   11.70649(14)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1850
_cell_measurement_theta_min      5.3710
_cell_volume                     954.47(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.231
_diffrn_reflns_theta_min         5.397
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    26.341
_exptl_absorpt_correction_T_max  0.500
_exptl_absorpt_correction_T_min  0.180
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.130
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.609
_refine_diff_density_min         -2.765
_refine_diff_density_rms         0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0557P)^2^+1.4931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0826
_refine_special_details
;
The maximum and minimum residual electron density peaks of 0.61 and 2.76
e/ang3 are located 1.35 and 0.83 ang, respectively, from the I1 atom.
;
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             1964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01165d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245680
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.088
_shelx_estimated_absorpt_t_max   0.119
_shelx_res_checksum              28123
_shelx_hkl_checksum              2294