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_7251594
_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         'C26.9 H14.9 F6 N O, 0.1(C)'
_chemical_formula_sum            'C27 H14.9 F6 N O'
_chemical_formula_weight         483.30
_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             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                106.652(2)
_cell_angle_beta                 94.045(2)
_cell_angle_gamma                99.828(2)
_cell_formula_units_Z            6
_cell_length_a                   14.0330(3)
_cell_length_b                   14.9961(3)
_cell_length_c                   15.6184(3)
_cell_measurement_reflns_used    16980
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.7420
_cell_measurement_theta_min      1.9250
_cell_volume                     3077.75(12)
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -45.00  65.00   0.50   21.43    --  -13.34  36.00 129.00  220
  2  \w     31.00  68.00   0.50   21.43    --   12.72  57.00  30.00   74
  3  \w     42.00  76.00   0.50   21.43    --   12.72 178.00 150.00   68
  4  \w     49.00  93.00   0.50   21.43    --   12.72 178.00 -60.00   88
  5  \w    -60.00  40.00   0.50   21.43    --   12.72 -57.00 -60.00  200
  6  \w    -22.00  17.00   0.50   21.43    --  -13.34 -99.00 -30.00   78
  7  \w    -23.00   7.00   0.50   21.43    --  -13.34 -99.00-150.00   60
  8  \w    -94.00  -9.00   0.50   21.43    --  -13.34 -36.00 -26.00  170
  9  \w    -21.00  32.00   0.50   21.43    --  -13.34 -99.00 120.00  106
;
_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      -0.0427394000
_diffrn_orient_matrix_UB_12      -0.0216115000
_diffrn_orient_matrix_UB_13      0.0137992000
_diffrn_orient_matrix_UB_21      -0.0123907000
_diffrn_orient_matrix_UB_22      0.0451278000
_diffrn_orient_matrix_UB_23      0.0172585000
_diffrn_orient_matrix_UB_31      -0.0263463000
_diffrn_orient_matrix_UB_32      -0.0059206000
_diffrn_orient_matrix_UB_33      -0.0423708000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37387
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.674
_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    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             1475
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     961
_refine_ls_number_reflns         12595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1062P)^2^+2.8645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9417
_reflns_number_total             12595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09266c2.cif
_cod_data_source_block           mm1-139_2
_cod_original_cell_volume        3077.75(11)
_cod_original_formula_sum        'C27 H14.90 F6 N O'
_cod_database_code               7251594
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C27 H15 F6 N1 O1'
_diffrn_oxdiff_digest_hkl
;
0183d800f0b2c02d5e4eba8ab166d8df0e82cd
;
_reflns_odcompleteness_completeness 99.96
_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. Others
 Fixed Sof: C02I(0.9) H02I(0.9) C02Q(0.9) H02Q(0.9) C02W(0.9) H02W(0.9)
 C1(0.1) C2(0.1) C3(0.1)
3.a Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00W(H00W), C00X(H00X), C00Z(H00Z), C017(H017), C019(H019),
 C01B(H01B), C01D(H01D), C01E(H01E), C01G(H01G), C01I(H01I), C01J(H01J),
 C01L(H01L), C01Q(H01Q), C01S(H01S), C01V(H01V), C01W(H01W), C021(H021),
 C022(H022), C023(H023), C024(H024), C025(H025), C027(H027), C028(H028),
 C02A(H02A), C02B(H02B), C02C(H02C), C02D(H02D), C02G(H02G), C02I(H02I),
 C02K(H02K), C02L(H02L), C02M(H02M), C02O(H02O), C02Q(H02Q), C02R(H02R),
 C02S(H02S), C02T(H02T), C02U(H02U), C02V(H02V), C02W(H02W), C02X(H02X)
3.b Idealised tetrahedral OH refined as rotating group:
 O00G(H00G), O00J(H00J), O00L(H00L)
;
_shelx_res_checksum              29452
_olex2_date_sample_completion    2025-11-03
_olex2_date_sample_data_collection 2021-01-21
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.876