Fluorinated tolane-based fluorophores bearing a branched flexible unit with aggregation-induced emission enhancement characteristics
Yamada, Shigeyuki; Sato, Masaya; Uto, Eiji; Kataoka, Mitsuki; Morita, Masato; Konno, Tsutomu; New Journal of Chemistry 46 (2022) 3392–3400; doi:10.1039/D1NJ05822C

data_7061243
_publ_section_title
;
 Fluorinated tolane-based fluorophores bearing a branched flexible unit
 with aggregation-induced emission enhancement characteristics
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3392
_journal_page_last               3400
_journal_paper_doi               10.1039/D1NJ05822C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C23 H15 F5 O2'
_chemical_formula_sum            'C23 H15 F5 O2'
_chemical_formula_weight         418.35
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-30
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                88.321(4)
_cell_angle_beta                 83.008(4)
_cell_angle_gamma                84.421(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9679(5)
_cell_length_b                   9.2898(4)
_cell_length_c                   11.8018(5)
_cell_measurement_reflns_used    5939
_cell_measurement_temperature    299
_cell_measurement_theta_max      27.1360
_cell_measurement_theta_min      2.1640
_cell_volume                     971.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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      299
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_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     40.00  75.00   0.25    0.73    --    5.00  76.00-180.00  140
  2  \w     44.00  72.00   0.25    0.73    --    5.00  57.00 -30.00  112
  3  \w     -9.00  27.00   0.25    0.73    --    5.00  76.00-180.00  144
  4  \w    -47.00 -10.00   0.25    0.73    --  -11.80  57.00  60.00  148
  5  \w    -46.00  24.00   0.25    0.73    --  -11.80  57.00 -60.00  280
  6  \w    -48.00   8.00   0.25    0.73    --  -11.80  76.00  90.00  224
  7  \w    -53.00  68.00   0.25    0.73    --  -11.80  76.00 150.00  484
  8  \w    -88.00  75.00   0.25    0.73    --  -11.80  -1.00 120.00  652
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0154908000
_diffrn_orient_matrix_UB_12      -0.0206802000
_diffrn_orient_matrix_UB_13      0.0582570000
_diffrn_orient_matrix_UB_21      -0.0094437000
_diffrn_orient_matrix_UB_22      -0.0710863000
_diffrn_orient_matrix_UB_23      -0.0164042000
_diffrn_orient_matrix_UB_31      0.0779598000
_diffrn_orient_matrix_UB_32      -0.0201559000
_diffrn_orient_matrix_UB_33      0.0021580000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14654
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.203
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.713
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.335
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0700P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3115
_reflns_number_total             4447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05822c2.cif
_cod_data_source_block           tol-5f-mande-s
_cod_depositor_comments
'Adding full bibliography for 7061242--7061245.cif.'
_cod_database_code               7061243
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C23H15F5O2
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00O(H00O),
 C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00G,H00H,H00K)
;
_shelx_res_checksum              10520
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.575