Fluorescent-state switching of a 10-hydroxybezo[h]quinoline skeleton through the electronic nature of substituents
Miwa, Marino; Ito, Akitaka; RSC Advances 16 (2026) 8453–8465; doi:10.1039/D5RA09266C

data_7251595
_publ_section_title
;
 Fluorescent-state switching of a 10-hydroxybezo[h]quinoline skeleton
 through the electronic nature of substituents
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              8453
_journal_page_last               8465
_journal_paper_doi               10.1039/D5RA09266C
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C25 H15 F2 N O'
_chemical_formula_sum            'C25 H15 F2 N O'
_chemical_formula_weight         383.38
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2025-11-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-11-24 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.115(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8336(2)
_cell_length_b                   20.9976(9)
_cell_length_c                   10.5840(4)
_cell_measurement_reflns_used    3595
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.8250
_cell_measurement_theta_min      1.9500
_cell_volume                     851.39(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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    -49.00 -21.00   0.50    4.68    --   12.40 -65.00 -32.00   56
  2  \w    -18.00  33.00   0.50    4.68    --   12.40 -65.00 -32.00  102
  3  \w      7.00  32.00   0.50    4.68    --  -13.03 -99.00-180.00   50
  4  \w     -3.00  88.00   0.50    4.68    --   12.40  65.00 103.00  182
  5  \w     44.00  94.00   0.50    4.68    --   12.40 178.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362065000
_diffrn_orient_matrix_UB_12      -0.0207464000
_diffrn_orient_matrix_UB_13      -0.0507799000
_diffrn_orient_matrix_UB_21      -0.1651387000
_diffrn_orient_matrix_UB_22      -0.0146641000
_diffrn_orient_matrix_UB_23      0.0059293000
_diffrn_orient_matrix_UB_31      -0.0754385000
_diffrn_orient_matrix_UB_32      0.0222885000
_diffrn_orient_matrix_UB_33      -0.0433590000
_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  0.0149
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4865
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.156
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.887
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.7029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.802
_reflns_number_gt                2844
_reflns_number_total             3141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09266c2.cif
_cod_data_source_block           mm1-146_1
_cod_database_code               7251595
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C52 H28 N4 O4 '
_diffrn_oxdiff_digest_frames
;
01e55a593d78793659e69d28ba15584a1d00490bfdf
;
_diffrn_oxdiff_digest_hkl
;
0119814d832d0295d1c08503689b25437ad713
;
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C15(H15), C18(H18), C19(H19), C1A(H1A), C1B(H1B),
 C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C1G(H1G), C1H(H1H)
2.b Idealised tetrahedral OH refined as rotating group:
 O9(H9)
;
_olex2_date_sample_completion    2021-02-01
_olex2_date_sample_data_collection 2021-02-01
_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 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.814