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_7251591
_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         'C29 H27 N3 O, 0.25(C2 H3 N)'
_chemical_formula_sum            'C29.5 H27.75 N3.25 O'
_chemical_formula_weight         443.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                90
_cell_angle_beta                 105.179(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9713(7)
_cell_length_b                   9.4358(3)
_cell_length_c                   27.1606(11)
_cell_measurement_reflns_used    9078
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      30.0850
_cell_measurement_theta_min      2.2370
_cell_volume                     4692.4(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -81.00  10.00   0.50    7.84    --  -13.34 -60.00-143.00  182
  2  \w    -33.00  60.00   0.50    7.84    --  -13.34  60.00  -3.00  186
  3  \w     46.00  74.00   0.50    7.84    --   12.72 178.00-120.00   56
  4  \w     45.00  83.00   0.50    7.84    --   12.72 178.00-150.00   76
;
_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      0.0318127000
_diffrn_orient_matrix_UB_12      0.0150236000
_diffrn_orient_matrix_UB_13      -0.0081598000
_diffrn_orient_matrix_UB_21      0.0196505000
_diffrn_orient_matrix_UB_22      -0.0514206000
_diffrn_orient_matrix_UB_23      0.0172454000
_diffrn_orient_matrix_UB_31      -0.0101019000
_diffrn_orient_matrix_UB_32      -0.0527383000
_diffrn_orient_matrix_UB_33      -0.0191803000
_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  0.0201
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13150
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.848
_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    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1884
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0489P)^2^+3.9603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4062
_reflns_number_total             4765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09266c2.cif
_cod_data_source_block           mm2-103_2
_cod_original_formula_sum        'C29.50 H27.75 N3.25 O'
_cod_database_code               7251591
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C29 H27 N3 O1'
_diffrn_oxdiff_digest_hkl
;
016ca806661a7ade5dc9e21357376106be3e89
;
_reflns_odcompleteness_completeness 99.43
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N4-C31
 1.14 with sigma of 0.02
 C36-C34 = C37-C36 = C38-C37
 1.39 with sigma of 0.01
 C30-N4
 2.593 with sigma of 0.02
 C19-C34 = C20-C33 = C35-C32
 2.8 with sigma of 0.01
 C31-N4
 1.137 with sigma of 0.01
 C31-C30
 1.456 with sigma of 0.01
 O7-C21
 1.42 with sigma of 0.01
 N4-C30
 2.59 with sigma of 0.04
 C26-C20 \\sim C35-C20
 with sigma of 0.01
 C20-C19 \\sim C35-C20 \\sim C35-C34 \\sim C34-C33 \\sim C33-C32 \\sim C32-C19
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O7 \\sim C23 \\sim C21 \\sim C20 \\sim C19 \\sim O1 \\sim C32 \\sim C33 \\sim
N3 \\sim C34 \\sim C26 \\sim C35 \\sim N5 \\sim C25 \\sim C24 \\sim C38 \\sim
C27 \\sim C37 \\sim C28 \\sim C36 \\sim C29: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 O7, C23, C21, C20, C19, O1, C32, C33, N3, C34, C26, C35, N5, C25, C24, C38,
 C27, C37, C28, C36, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4, C31, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O7)=Sof(H7A)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C35)=Sof(C34)=
 Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(N5)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(N3)=Sof(C25)=Sof(C26)=Sof(C27)=Sof(H27)=Sof(C29)=
 Sof(H29)=Sof(C28)=Sof(H28)=Sof(C24)=Sof(H24)=Sof(O1)=Sof(H1)=FVAR(1)
 Fixed Sof: N4(0.25) C31(0.25) C30(0.25) H30A(0.25) H30B(0.25) H30C(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C17(H17), C16(H16), C12(H12), C15(H15), C13(H13), C5(H5), C4(H4),
 C7(H7), C8(H8), C27(H27), C29(H29), C28(H28), C24(H24), C32(H32), C33(H33),
 C36(H36), C37(H37), C38(H38)
6.b Fitted hexagon refined as free rotating group:
 C35(C34,C36,C37,C38,N5)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C30(H30A,H30B,H30C)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O7(H7A)
;
_shelx_res_checksum              19387
_olex2_date_sample_completion    2021-07-26
_olex2_date_sample_data_collection 2021-07-12
_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 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.945