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_7061245
_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         'C19 H11 F4 N O2'
_chemical_formula_sum            'C19 H11 F4 N O2'
_chemical_formula_weight         361.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.582(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1206(3)
_cell_length_b                   22.0913(10)
_cell_length_c                   11.8054(6)
_cell_measurement_reflns_used    5779
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.2160
_cell_measurement_theta_min      2.7690
_cell_volume                     1582.28(13)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_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      9.00  35.00   0.25    0.93    --    5.00  57.00  90.00  104
  2  \w     41.00  71.00   0.25    0.93    --    5.00  57.00  90.00  120
  3  \w    -50.00  24.00   0.25    0.93    --  -11.80  76.00 150.00  296
  4  \w     29.00  76.00   0.25    0.93    --  -11.80  76.00 150.00  188
  5  \w     -5.00  74.00   0.25    0.93    --  -11.80  76.00-120.00  316
  6  \w    -53.00  -9.00   0.25    0.93    --  -11.80  76.00-120.00  176
;
_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      -0.0013850000
_diffrn_orient_matrix_UB_12      -0.0309209000
_diffrn_orient_matrix_UB_13      -0.0162152000
_diffrn_orient_matrix_UB_21      -0.0054687000
_diffrn_orient_matrix_UB_22      -0.0086081000
_diffrn_orient_matrix_UB_23      0.0574374000
_diffrn_orient_matrix_UB_31      -0.1168073000
_diffrn_orient_matrix_UB_32      0.0007999000
_diffrn_orient_matrix_UB_33      -0.0104356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83662
_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    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0736P)^2^+0.2798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2663
_reflns_number_total             3607
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05822c2.cif
_cod_data_source_block           rac-cn
_cod_depositor_comments
'Adding full bibliography for 7061242--7061245.cif.'
_cod_database_code               7061245
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H11F4NO2
_reflns_odcompleteness_completeness 99.60
_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
2.a Ternary CH refined with riding coordinates:
 C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00P(H00C,H00D), C00Q(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K)
;
_shelx_res_checksum              34246
_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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.636