Fluorine-induced emission enhancement of tolanes via formation of tight molecular aggregates
Morita, Masato; Yamada, Shigeyuki; Konno, Tsutomu; New Journal of Chemistry 44 (2020) 6704–6708; doi:10.1039/D0NJ01268H

data_7059494
_publ_section_title
;
 Fluorine-induced emission enhancement of tolanes via formation of tight
 molecular aggregates
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6704
_journal_page_last               6708
_journal_paper_doi               10.1039/D0NJ01268H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H7 F4 N O'
_chemical_formula_sum            'C16 H7 F4 N O'
_chemical_formula_weight         305.23
_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             2020-01-29
_audit_creation_method
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                95.911(2)
_cell_angle_beta                 90.746(3)
_cell_angle_gamma                98.579(3)
_cell_formula_units_Z            4
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_cell_length_c                   28.6607(8)
_cell_measurement_reflns_used    7674
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.5090
_cell_measurement_theta_min      2.6510
_cell_volume                     1360.15(9)
_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 0.999
_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    -13.00  13.00   0.25    2.95    --    5.00  76.00 -30.00  104
  2  \w    -53.00  22.00   0.25    2.95    --  -11.60  76.00 120.00  300
  3  \w    -47.00  -2.00   0.25    2.95    --  -11.60  57.00  30.00  180
  4  \w    -48.00  58.00   0.25    2.95    --  -11.60  38.00-120.00  424
  5  \w    -53.00  78.00   0.25    2.95    --  -11.60  76.00 -90.00  524
  6  \w   -101.00   8.00   0.25    2.95    --  -11.60   0.00 -90.00  436
;
_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      0.1062914000
_diffrn_orient_matrix_UB_12      0.0115977000
_diffrn_orient_matrix_UB_13      0.0100657000
_diffrn_orient_matrix_UB_21      0.0438925000
_diffrn_orient_matrix_UB_22      0.0059569000
_diffrn_orient_matrix_UB_23      -0.0225843000
_diffrn_orient_matrix_UB_31      0.0013948000
_diffrn_orient_matrix_UB_32      0.0923387000
_diffrn_orient_matrix_UB_33      0.0028603000
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            18706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.144
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67928
_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    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0422
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4012
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01268h2.cif
_cod_data_source_block           c1_4f_cn
_cod_depositor_comments
;Adding full bibliography for 7059490--7059495.cif.

 Adding full bibliography for 7059490--7059495.cif.
;
_cod_database_code               7059494
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H7F4NO
_reflns_odcompleteness_completeness 99.58
_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:
 C00K(H00K), C00N(H00N), C00P(H00P), C00Q(H00Q), C00W(H00W), C00X(H00X),
 C011(H011), C014(H014)
2.b Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C), C018(H01D,H01E,H01F)
;
_shelx_res_checksum              56238
_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 1.770
_oxdiff_exptl_absorpt_empirical_full_min 0.591