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_7248876
_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         'C7 H8 N4 O2, C6 F4 I2'
_chemical_formula_sum            'C13 H8 F4 I2 N4 O2'
_chemical_formula_weight         582.03
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_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             2024-04-16T16:20:29-00:00
_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                90
_cell_angle_beta                 113.293(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.924(8)
_cell_length_b                   4.4267(18)
_cell_length_c                   20.419(8)
_cell_measurement_reflns_used    5504
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.23
_cell_measurement_wavelength     0.71073
_cell_volume                     1654.1(12)
_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-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_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      0.000546
_diffrn_orient_matrix_UB_12      0.223173
_diffrn_orient_matrix_UB_13      0.007785
_diffrn_orient_matrix_UB_21      0.049063
_diffrn_orient_matrix_UB_22      -0.017383
_diffrn_orient_matrix_UB_23      0.040161
_diffrn_orient_matrix_UB_31      0.024053
_diffrn_orient_matrix_UB_32      0.030391
_diffrn_orient_matrix_UB_33      -0.034197
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32965
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_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         28.019
_diffrn_reflns_theta_min         1.837
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.86
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0269P)^2^+1.5962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0
_reflns_number_gt                3083
_reflns_number_total             3979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00138a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7248876--7248878.cif.'
_cod_original_cell_volume        1654.1(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248876
_shelx_estimated_absorpt_t_min   0.411
_shelx_estimated_absorpt_t_max   0.927
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              8631