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_7245224
_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         'C6 F4 I2, 4(C15 H12)'
_chemical_formula_sum            'C66 H48 F4 I2'
_chemical_formula_weight         1170.84
_chemical_name_systematic        'I2F4:MA 1:4'
_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   geom
_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
;
2022-04-12 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                97.450(4)
_cell_angle_beta                 103.319(5)
_cell_angle_gamma                98.140(5)
_cell_formula_units_Z            1
_cell_length_a                   8.1105(5)
_cell_length_b                   10.3429(5)
_cell_length_c                   16.2211(8)
_cell_measurement_reflns_used    3484
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.2540
_cell_measurement_theta_min      3.5620
_cell_volume                     1292.05(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -39.00  46.00   1.00    5.51    --   17.77 -77.00 -90.00   85
  2  \w     -8.00  20.00   1.00    5.51    --   17.77  77.00  30.00   28
  3  \w     -4.00  32.00   1.00    5.51    --   17.77  77.00-120.00   36
  4  \w      0.00  35.00   1.00    5.51    --   17.77  77.00 120.00   35
  5  \w    -50.00  35.00   1.00    5.51    --   17.77 -38.00 120.00   85
  6  \w    -51.00  36.00   1.00    5.51    --   17.77 -57.00  30.00   87
;
_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      0.0911754000
_diffrn_orient_matrix_UB_12      0.0104058000
_diffrn_orient_matrix_UB_13      0.0134974000
_diffrn_orient_matrix_UB_21      0.0035492000
_diffrn_orient_matrix_UB_22      0.0682500000
_diffrn_orient_matrix_UB_23      -0.0025277000
_diffrn_orient_matrix_UB_31      -0.0038349000
_diffrn_orient_matrix_UB_32      0.0131535000
_diffrn_orient_matrix_UB_33      0.0434697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8611
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97806
_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    1.505
_exptl_crystal_description       plate
_exptl_crystal_F_000             586
_exptl_crystal_preparation       '1:4 BM 90 min at 20 Hz'
_exptl_crystal_recrystallization_method 'Slow evaporation Chloroform:Ethanol'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0029(4)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+1.9755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             4551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00720g2.cif
_cod_data_source_block           (MA)4-I2F4
_cod_original_cell_volume        1292.05(12)
_cod_database_code               7245224
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.785
_shelx_estimated_absorpt_t_min   0.568
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C19, C16, H16, C17, C21, H17, C18, C20, H21, H18, C25, C22, C24, C26, H22,
 C23, C30, H26A, H26B, H26C, C27, C29, H30, H27, C28, H29, H28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, I1, C32, C31, C33, F1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C1, H1, C2, C6, H2, C3, C5, C7, H3, C4, C10, H7, C8, H4, C9, C11, C12,
 C15, H11A, H11B, H11C, H12, C14, H15, H13, H14
 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:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C30(H30)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              67080
_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 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.937