Synthesis and characterization of bent fluorine-containing donor-π-acceptor molecules as intense luminophores with large Stokes shifts.
Yamada, Shigeyuki; Nishizawa, Akito; Morita, Masato; Hosokai, Takuya; Okabayashi, Yusuke; Agou, Tomohiro; Hosoya, Takaaki; Kubota, Toshio; Konno, Tsutomu; Organic & biomolecular chemistry 17 (2019) 6911–6919; doi:10.1039/c9ob01300h

data_7156949
_publ_section_title
;
 Synthesis and characterization of bent fluorine-containing
 donor-\p-acceptor molecules as intense luminophores with large Stokes
 shifts.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6911
_journal_page_last               6919
_journal_paper_doi               10.1039/c9ob01300h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C35 H14 F14 O2'
_chemical_formula_sum            'C35 H14 F14 O2'
_chemical_formula_weight         732.46
_chemical_name_systematic
3,3,4,4,5,5-hexafluoro-1,2-bis[2,3,5,6-tetrafluoro-4-(2-(4-methoxyphenyl)ethyn-1-yl)phenyl]cyclopentene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-03-10 deposited with the CCDC.    2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2739(8)
_cell_length_b                   20.464(3)
_cell_length_c                   23.723(3)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8040
_cell_measurement_theta_min      2.1050
_cell_volume                     3045.8(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.1653
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.984
_diffrn_source                   'Rigaku VariMax Mo'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1464
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/CH2Cl2 (1/1)'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 470 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   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5375
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0816
_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^)+(0.0936P)^2^+1.6369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.2656
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2296
_reflns_number_total             5375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01300h2.cif
_cod_data_source_block           yamada1
_cod_depositor_comments
'Adding full bibliography for 7156949--7156950.cif.'
_cod_database_code               7156949
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.984
_oxdiff_exptl_absorpt_empirical_full_min 0.511
_oxdiff_exptl_absorpt_empirical_full_max 11.947
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              40812