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_7248878
_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(C8 H10 N4 O2), 0.5(C6 F4 I2)'
_chemical_formula_sum            'C19 H20 F2 I N8 O4'
_chemical_formula_weight         589.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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             2024-05-16T09:45:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-05-16 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.90(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.904(18)
_cell_length_b                   4.044(4)
_cell_length_c                   25.87(2)
_cell_measurement_reflns_used    493
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13.14
_cell_measurement_theta_min      6.69
_cell_measurement_wavelength     0.71073
_cell_volume                     2141(3)
_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 0.982
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.017438
_diffrn_orient_matrix_UB_12      0.071834
_diffrn_orient_matrix_UB_13      0.026964
_diffrn_orient_matrix_UB_21      -0.030134
_diffrn_orient_matrix_UB_22      0.003628
_diffrn_orient_matrix_UB_23      0.005808
_diffrn_orient_matrix_UB_31      0.007073
_diffrn_orient_matrix_UB_32      -0.16164
_diffrn_orient_matrix_UB_33      0.012113
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3691
_diffrn_reflns_av_unetI/netI     0.1599
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            58277
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.982
_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         28.944
_diffrn_reflns_theta_min         1.623
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10
;
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.97
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0294P)^2^] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0
_reflns_number_gt                2720
_reflns_number_total             5576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00138a2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7248876--7248878.cif.'
_cod_original_cell_volume        2140(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248878
_shelx_estimated_absorpt_t_min   0.635
_shelx_estimated_absorpt_t_max   0.912
_shelx_res_checksum              65876