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_7245222
_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, C15 H12'
_chemical_formula_sum            'C21 H12 F4 I2'
_chemical_formula_weight         594.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_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
;
2022-04-12 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.826(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2375(10)
_cell_length_b                   8.1987(3)
_cell_length_c                   16.1855(12)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4280
_cell_measurement_theta_min      4.0970
_cell_volume                     1954.7(2)
_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      293(2)
_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     -8.00  18.00   1.00    6.94    --   17.92  77.00 120.00   26
  2  \w    -43.00  79.00   1.00    4.00    --   17.92   0.00   0.00  122
  3  \w     12.00  86.00   1.00    4.00    --   17.92  57.00  30.00   74
;
_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      0.0000253000
_diffrn_orient_matrix_UB_12      0.0001817000
_diffrn_orient_matrix_UB_13      0.0438381000
_diffrn_orient_matrix_UB_21      0.0441477000
_diffrn_orient_matrix_UB_22      0.0344989000
_diffrn_orient_matrix_UB_23      0.0105379000
_diffrn_orient_matrix_UB_31      -0.0191901000
_diffrn_orient_matrix_UB_32      0.0793467000
_diffrn_orient_matrix_UB_33      -0.0046728000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7713
_diffrn_reflns_point_group_measured_fraction_full 0.685
_diffrn_reflns_point_group_measured_fraction_max 0.685
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77555
_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    2.019
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.661(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     429
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0419P)^2^+0.3337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.372
_reflns_Friedel_fraction_full    0.371
_reflns_Friedel_fraction_max     0.371
_reflns_number_gt                3596
_reflns_number_total             4714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00720g2.cif
_cod_data_source_block           MA-I2F4
_cod_database_code               7245222
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.562
_shelx_estimated_absorpt_t_min   0.180
_reflns_odcompleteness_completeness 99.63
_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. Restrained distances
 H9-H7A
 2 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C1, H1, C2, H2, C3, H3, C4, H4, C5, C6, C7, H7A, H7B, H7C, C8, C9, H9, C10,
 H10, C11, H11, C12, H12, C13, C14, H14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 I1, I2, F3, F4, F1, F2, C16, C18, C20, C17, C19, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 I3, I4, F5, F7, F6, F8, C40, C38, C41, C42, C37, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C36, C28, H28A, H28B, H28C, C24, H24, C32, H32, C26, C30, H30, C34, C22, H22,
 C23, H23, C25, H25, C27, C29, C31, H31, C33, H33, C35, H35
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C32(H32), C30(H30), C22(H22), C1(H1), C2(H2), C3(H3), C4(H4),
 C23(H23), C25(H25), C31(H31), C9(H9), C33(H33), C10(H10), C35(H35), C11(H11),
 C12(H12), C14(H14)
4.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              35126
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.777