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_7237744
_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 H16 F4'
_chemical_formula_sum            'C26 H16 F4'
_chemical_formula_weight         404.39
_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                 108.037(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9748(6)
_cell_length_b                   9.6537(6)
_cell_length_c                   11.0118(7)
_cell_measurement_reflns_used    2878
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2590
_cell_measurement_theta_min      3.8150
_cell_volume                     1008.26(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -52.00   43.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569  -77.0000   60.0000 95

  2 omega  -11.00   83.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569   77.0000 -180.0000 94

  3 omega   -1.00   83.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569   57.0000  120.0000 84

  4 omega   35.00   88.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569  178.0000   60.0000 53

  5 omega  -25.00   55.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569  -99.0000  -90.0000 80

  6 omega  -84.00    0.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9507  -57.0000 -150.0000 84

  7 omega   32.00   88.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569 -178.0000 -120.0000 56

  8 omega  -53.00   39.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569    0.0000   90.0000 92

  9 omega   -3.00   85.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569   37.0000   30.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0737819000
_diffrn_orient_matrix_UB_12      -0.0088055000
_diffrn_orient_matrix_UB_13      -0.0278517000
_diffrn_orient_matrix_UB_21      -0.0049989000
_diffrn_orient_matrix_UB_22      0.0672775000
_diffrn_orient_matrix_UB_23      -0.0270177000
_diffrn_orient_matrix_UB_31      0.0111707000
_diffrn_orient_matrix_UB_32      -0.0282359000
_diffrn_orient_matrix_UB_33      -0.0555093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13939
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.204
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 552 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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.1113
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2813
_refine_ls_wR_factor_ref         0.3482
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1994
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc00511k2.cif
_cod_data_source_block           171124_ny_zh25
_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_original_cell_volume        1008.26(11)
_cod_database_code               7237744
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H F'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F2, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 F3, C23
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C12, C13
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C18, C19
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C25) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C26(H26), C8(H8), C16(H16), C14(H14), C4(H4), C11(H11), C19(H19),
 C7(H7), C18(H18), C22(H22), C10(H10), C13(H13), C24(H24), C25(H25), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'