Assembling photoactive materials from polycyclic aromatic hydrocarbons (PAHs): room temperature phosphorescence and excimer-emission in co-crystals with 1,4-diiodotetrafluorobenzene
Azzali, Alessandra; d'Agostino, Simone; Capacci, Mattia; Spinelli, Floriana; Ventura, Barbara; Grepioni, Fabrizia; CrystEngComm  (2022) –; doi:10.1039/D2CE00720G

data_7245223
_publ_section_title
;
 Assembling photoactive materials from polycyclic aromatic hydrocarbons
 (PAHs): room temperature phosphorescence and excimer-emission in
 co-crystals with 1,4-diiodotetrafluorobenzene
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00720G
_journal_year                    2022
_chemical_formula_moiety         '2(C6 F4 I2), C14 H10'
_chemical_formula_sum            'C26 H10 F8 I4'
_chemical_formula_weight         981.94
_chemical_name_systematic        A(I2F4)2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                73.604(8)
_cell_angle_beta                 89.751(6)
_cell_angle_gamma                81.821(7)
_cell_formula_units_Z            1
_cell_length_a                   5.9997(4)
_cell_length_b                   9.7209(10)
_cell_length_c                   12.2681(10)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    300
_cell_measurement_theta_max      29.0620
_cell_measurement_theta_min      3.7930
_cell_volume                     678.94(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -1.00  86.00   1.00    1.00    --   18.00  57.00  90.00   87
  2  \w     -8.00  21.00   1.00    2.50    --   18.00  77.00-180.00   29
  3  \w    -10.00  38.00   1.00    2.50    --   18.00  77.00 -60.00   48
  4  \w    -46.00  35.00   1.00    2.50    --   18.00 -57.00-180.00   81
  5  \w     -4.00  86.00   1.00    2.50    --   18.00  38.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091922000
_diffrn_orient_matrix_UB_12      -0.0639728000
_diffrn_orient_matrix_UB_13      -0.0176802000
_diffrn_orient_matrix_UB_21      0.0684441000
_diffrn_orient_matrix_UB_22      0.0308520000
_diffrn_orient_matrix_UB_23      -0.0450136000
_diffrn_orient_matrix_UB_31      0.0975520000
_diffrn_orient_matrix_UB_32      -0.0294697000
_diffrn_orient_matrix_UB_33      0.0360353000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3944
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.295
_diffrn_reflns_theta_max         24.295
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             450
_exptl_crystal_preparation       'Ball Milling 90 min'
_exptl_crystal_recrystallization_method
'Slow evaporation from Chloroform:EtOH 50:50'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0246P)^2^+0.3710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0633
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00720g2.cif
_cod_data_source_block           A-(I2F4)2
_cod_database_code               7245223
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.707
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C10, I1, C13, C8, C12, F1, C9, F3, C11, F2, F4, I2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, C1, H1, C2, C6, H2, C5, H3, C4, C7, H4, H7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_shelx_res_checksum              13176
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.713