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_7059491
_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 H11 N O'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-27
_audit_creation_method
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.747(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0792(3)
_cell_length_b                   7.7395(3)
_cell_length_c                   28.2605(15)
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8440
_cell_measurement_theta_min      2.7010
_cell_volume                     1273.26(11)
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     -2.00  24.00   0.25    3.84    --  -11.80  57.00  22.00  104
  2  \w    -47.00 -10.00   0.25    3.84    --  -11.80  57.00  22.00  148
  3  \w    -84.00  92.00   0.25    3.84    --    5.00  19.00 -60.00  704
  4  \w      8.00  33.00   0.25    3.84    --    5.00  57.00  22.00  100
  5  \w      0.00  26.00   0.25    3.84    --  -11.80  57.00 -60.00  104
  6  \w    -47.00  71.00   0.25    3.84    --  -11.80  57.00  90.00  472
  7  \w    -36.00 -10.00   0.25    3.84    --  -11.80  57.00 -60.00  104
;
_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      0.0577469000
_diffrn_orient_matrix_UB_12      -0.0411841000
_diffrn_orient_matrix_UB_13      -0.0154479000
_diffrn_orient_matrix_UB_21      -0.0683515000
_diffrn_orient_matrix_UB_22      0.0467532000
_diffrn_orient_matrix_UB_23      -0.0206144000
_diffrn_orient_matrix_UB_31      0.0827509000
_diffrn_orient_matrix_UB_32      0.0671333000
_diffrn_orient_matrix_UB_33      0.0048734000
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14685
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53065
_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    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.671
_exptl_crystal_size_mid          0.584
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0755P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2005
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01268h2.cif
_cod_data_source_block           c1-4h-cn
_cod_depositor_comments
;Adding full bibliography for 7059490--7059495.cif.

 Adding full bibliography for 7059490--7059495.cif.
;
_cod_database_code               7059491
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H11NO
_reflns_odcompleteness_completeness 99.74
_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:
 C006(H006), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00G,H00H)
;
_shelx_res_checksum              9100
_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.405