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_7245681
_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                 100.6098(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.84010(11)
_cell_length_b                   7.44774(7)
_cell_length_c                   11.95687(12)
_cell_measurement_reflns_used    9386
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1700
_cell_measurement_theta_min      3.7210
_cell_volume                     948.826(17)
_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 0.997
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.228
_diffrn_reflns_theta_min         4.149
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    26.498
_exptl_absorpt_correction_T_max  0.363
_exptl_absorpt_correction_T_min  0.061
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.8858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0659
_refine_special_details
;
The maximum and minimum residual electron density peaks of 0.70 and 0.91
e/ang3 are located 1.27 and 0.78 ang from the I1 atom, respectively.
;
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1937
_reflns_number_total             1958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01165d2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_cell_volume        948.826(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245681
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.078
_shelx_estimated_absorpt_t_max   0.223
_shelx_res_checksum              33023
_shelx_hkl_checksum              37114