Halogen atom effect of fluorinated tolanes on their luminescence characteristics
Morita, Masato; Yamada, Shigeyuki; Konno, Tsutomu; New Journal of Chemistry 46 (2022) 4562–4569; doi:10.1039/D1NJ05539A

data_7061211
_publ_section_title
;
 Halogen atom effect of fluorinated tolanes on their luminescence
 characteristics
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4562
_journal_page_last               4569
_journal_paper_doi               10.1039/D1NJ05539A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C15 H7 Cl F4 O'
_chemical_formula_sum            'C15 H7 Cl F4 O'
_chemical_formula_weight         314.66
_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             2020-12-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-21 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.733(3)
_cell_angle_beta                 92.011(3)
_cell_angle_gamma                97.051(4)
_cell_formula_units_Z            4
_cell_length_a                   6.2618(3)
_cell_length_b                   7.4426(3)
_cell_length_c                   29.3159(10)
_cell_measurement_reflns_used    7188
_cell_measurement_temperature    299
_cell_measurement_theta_max      29.6470
_cell_measurement_theta_min      2.7000
_cell_volume                     1354.87(10)
_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      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     48.00  74.00   0.25    4.67    --    5.00  76.00-150.00  104
  2  \w     -5.00  21.00   0.25    4.67    --    5.00  76.00-150.00  104
  3  \w    -53.00  30.00   0.25    4.67    --  -11.60  76.00  30.00  332
  4  \w    -53.00  24.00   0.25    4.67    --  -11.60  76.00 120.00  308
  5  \w     52.00  77.00   0.25    4.67    --  -11.60  38.00   0.00  100
  6  \w     11.00  78.00   0.25    4.67    --  -11.60  57.00 -90.00  268
  7  \w    -47.00  20.00   0.25    4.67    --  -11.60  57.00 -60.00  268
  8  \w    -53.00  78.00   0.25    4.67    --  -11.60  76.00-180.00  524
  9  \w     53.00  78.00   0.25    4.67    --  -11.60  76.00  30.00  100
;
_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      0.0121154000
_diffrn_orient_matrix_UB_12      0.0028711000
_diffrn_orient_matrix_UB_13      0.0241552000
_diffrn_orient_matrix_UB_21      -0.0580378000
_diffrn_orient_matrix_UB_22      -0.0878423000
_diffrn_orient_matrix_UB_23      0.0009455000
_diffrn_orient_matrix_UB_31      0.0976211000
_diffrn_orient_matrix_UB_32      -0.0387262000
_diffrn_orient_matrix_UB_33      -0.0013889000
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            19816
_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         27.480
_diffrn_reflns_theta_min         2.086
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57270
_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    1.543
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0707
_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^)+(0.1420P)^2^+0.1516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2179
_refine_ls_wR_factor_ref         0.2402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3901
_reflns_number_total             6184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05539a2.cif
_cod_data_source_block           c1-4f-cl
_cod_depositor_comments
'Adding full bibliography for 7061211--7061213.cif.'
_cod_database_code               7061211
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H7ClF4O
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00L(H00L), C00N(H00N), C00V(H00V), C00X(H00X),
 C00Y(H00Y), C012(H012)
2.b Idealised Me refined as rotating group:
 C010(H01D,H01E,H01F), C016(H01A,H01B,H01C)
;
_shelx_res_checksum              32331
_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 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.430