Fluorination of the tetraphenylethene core: synthesis, aggregation-induced emission, reversible mechanofluorochromism and thermofluorochromism of fluorinated tetraphenylethene derivatives
Zhang, Hao; Nie, Yong; Miao, Jinling; Zhang, Dengqing; Li, Yexin; Liu, Guangning; Sun, Guoxin; Jiang, Xuchuan; Journal of Materials Chemistry C 7 (2019) 3306–; doi:10.1039/C9TC00511K

data_7237747
_publ_section_title
;
 Fluorination of the tetraphenylethene core: synthesis,
 aggregation-induced emission, reversible mechanofluorochromism and
 thermofluorochromism of fluorinated tetraphenylethene derivatives
;
_journal_issue                   11
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3306
_journal_paper_doi               10.1039/C9TC00511K
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C26 H19 F'
_chemical_formula_sum            'C26 H19 F'
_chemical_formula_weight         350.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-05 deposited with the CCDC.	2019-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.740(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8507(6)
_cell_length_b                   9.6236(6)
_cell_length_c                   10.6312(7)
_cell_measurement_reflns_used    1722
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.768
_cell_measurement_theta_min      2.502
_cell_volume                     970.04(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4795
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.906
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 386 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0604
_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^)+(0.1169P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1901
_reflns_Friedel_coverage         0.336
_reflns_Friedel_fraction_full    0.378
_reflns_Friedel_fraction_max     0.378
_reflns_number_gt                1711
_reflns_number_total             2403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc00511k2.cif
_cod_data_source_block           170823b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7237747
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C15-C16 = C16-C17 = C17-C18 = C18-C19 = C19-C20 = C20-C15
 1.39 with sigma of 0.01
3. Rigid bond restraints
 C15, C16
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C16 \\sim C19 \\sim F1': within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1')
5. Others
 Sof(F1')=Sof(H5)=1-FVAR(1)
 Sof(F1)=Sof(H17)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'