On the role of torsional dynamics in the solid-state fluorescent properties of a new bifluorene–tetracarboxylic acid and its supramolecular assemblies: a structural and TD-DFT investigation
Podda, Enrico; Arca, Massimiliano; Pintus, Anna; Lippolis, Vito; Caltagirone, Claudia; Coles, Simon J.; Orton, James B.; Ennas, Guido; Picci, Giacomo; Davies, Robert P.; Aragoni, M. Carla; CrystEngComm 25 (2023) 1058–1066; doi:10.1039/D2CE01552H

data_7246140
_publ_section_title
;
 On the role of torsional dynamics in the solid-state fluorescent
 properties of a new bifluorene--tetracarboxylic acid and its
 supramolecular assemblies: a structural and TD-DFT investigation
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1058
_journal_page_last               1066
_journal_paper_doi               10.1039/D2CE01552H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C33 H24 O8'
_chemical_formula_sum            'C33 H24 O8'
_chemical_formula_weight         548.52
_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             2022-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-21 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                86.930(4)
_cell_angle_beta                 78.372(5)
_cell_angle_gamma                69.784(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9080(6)
_cell_length_b                   9.8092(5)
_cell_length_c                   17.5752(9)
_cell_measurement_reflns_used    7099
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.3910
_cell_measurement_theta_min      4.7670
_cell_volume                     1252.89(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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    -89.00  89.00   0.50    3.15    --    0.00   0.00-180.00  356
  2  \w    -89.00  89.00   0.50    3.15    --    0.00  59.00  30.00  356
  3  \w   -179.00  -1.00   0.50   12.62    --  -90.00  59.00  72.72  356
  4  \w   -179.00  -1.00   0.50   12.62    --  -90.00  59.00-167.89  356
  5  \w   -179.00  -1.00   0.50   12.62    --  -90.00  51.00 141.42  356
  6  \w   -179.00  -1.00   0.50   12.62    --  -90.00  57.00 -31.26  356
  7  \w   -179.00  -1.00   0.50   12.62    --  -90.00  10.00 120.00  356
  8  \w   -179.00  -1.00   0.50   12.62    --  -90.00  56.00  93.75  356
  9  \w   -178.00 -74.00   0.50   12.62    --  -90.00  30.00 -60.00  208
 10  \w   -179.00-122.00   0.50   12.62    --  -90.00  57.00  19.25  114
 11  \w    -90.00 -20.00   0.50   12.62    --  -90.00  57.00  19.25  140
 12  \w   -170.00-145.00   0.50   12.62    --  -90.00  57.00 -88.61   50
 13  \w    -71.00 -24.00   0.50   12.62    --  -90.00  57.00 -88.61   94
 14  \w    -63.00  -2.00   0.50   12.62    --  -90.00  10.00 120.00  122
 15  \w    -40.00 -12.00   0.50   12.62    --  -90.00  56.00  93.75   56
 16  \w   -179.00-153.00   0.50   12.62    --  -90.00  59.00 -37.28   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0425525000
_diffrn_orient_matrix_UB_12      -0.0920755000
_diffrn_orient_matrix_UB_13      0.0701700000
_diffrn_orient_matrix_UB_21      0.0349287000
_diffrn_orient_matrix_UB_22      -0.1277887000
_diffrn_orient_matrix_UB_23      -0.0552465000
_diffrn_orient_matrix_UB_31      0.2043942000
_diffrn_orient_matrix_UB_32      -0.0566665000
_diffrn_orient_matrix_UB_33      0.0059421000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18130
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.567
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0846P)^2^+0.5582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3563
_reflns_number_total             4549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01552h2.cif
_cod_data_source_block           2019ep010r1_1a
_cod_depositor_comments
'Adding full bibliography for 7246140--7246143.cif.'
_cod_database_code               7246140
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H24 O8'
_chemical_oxdiff_usercomment     372
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4-H4 = O8-H8 = O6-H6 = O2-H2
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C7(H7), C12(H12), C13(H13), C16(H16), C21(H21), C24(H24),
 C25(H25), C28(H28), C29(H29), C32(H32)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              94159
_shelx_hkl_checksum              86558
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.793