Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene: green synthesis, structure, photophysics and DFT studies
Benito, Mónica; Núñez, Rosario; Sinha, Sohini; Roscini, Claudio; Hidalgo-Rosa, Yoan; Schott, Eduardo; Zarate, Ximena; Molins, Elies; CrystEngComm 26 (2024) 3672–3686; doi:10.1039/D4CE00138A

data_7248877
_publ_section_title
;
 Methylxanthines for halogen bonded cocrystals with
 1,4-diiodotetrafluorobenzene: green synthesis, structure, photophysics
 and DFT studies
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              3672
_journal_page_last               3686
_journal_paper_doi               10.1039/D4CE00138A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C7 H8 N4 O2), C6 F4 I2'
_chemical_formula_sum            'C20 H16 F4 I2 N8 O4'
_chemical_formula_weight         762.21
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2024-04-16T16:28:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                82.022(8)
_cell_angle_beta                 88.669(8)
_cell_angle_gamma                80.671(9)
_cell_formula_units_Z            1
_cell_length_a                   4.0269(18)
_cell_length_b                   7.451(3)
_cell_length_c                   20.660(9)
_cell_measurement_reflns_used    2689
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      3.12
_cell_measurement_wavelength     0.71073
_cell_volume                     605.8(5)
_computing_cell_refinement       'SAINT V6.45A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      -0.146578
_diffrn_orient_matrix_UB_12      -0.096406
_diffrn_orient_matrix_UB_13      0.000402
_diffrn_orient_matrix_UB_21      0.036884
_diffrn_orient_matrix_UB_22      -0.000106
_diffrn_orient_matrix_UB_23      -0.048028
_diffrn_orient_matrix_UB_31      0.201215
_diffrn_orient_matrix_UB_32      -0.097766
_diffrn_orient_matrix_UB_33      0.009051
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12902
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.506
_diffrn_reflns_theta_min         1.991
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.673
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS - Bruker Nonius area detector scaling and absorption correction -
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.199
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.141
_reflns_Friedel_coverage         0
_reflns_number_gt                2106
_reflns_number_total             3074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00138a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7248876--7248878.cif.'
_cod_database_code               7248877
_shelx_estimated_absorpt_t_min   0.74
_shelx_estimated_absorpt_t_max   0.835
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              62444