Turn-off fluorescence sensing of benzenediols <i>via</i> guest-induced π-conjugation switching in bisimidazole-based hydrindacene allosteric receptors.
Kataoka, Takayuki; Tsuchido, Yoshitaka; Kawai, Hidetoshi; Physical chemistry chemical physics : PCCP 28 (2026) 2608–2614; doi:10.1039/d5cp04027b

data_7251711
_publ_section_title
;
 Turn-off fluorescence sensing of benzenediols <i>via</i> guest-induced
 &#x3c0;-conjugation switching in bisimidazole-based hydrindacene
 allosteric receptors.
;
_journal_issue                   3
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              2608
_journal_page_last               2614
_journal_paper_doi               10.1039/d5cp04027b
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C38 H38 N4 O8, 2(C H4 O)'
_chemical_formula_sum            'C40 H46 N4 O10'
_chemical_formula_weight         742.81
_chemical_name_common            Bis(benzimidazolyl)hydrindacene
_chemical_name_systematic        Benzimidazolyl_Hydrindacene
_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_block_doi                 10.5517/ccdc.csd.cc2j23b2
_audit_creation_date             2024-01-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2024-01-16 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.498(4)
_cell_angle_beta                 101.414(4)
_cell_angle_gamma                96.313(4)
_cell_formula_units_Z            1
_cell_length_a                   7.8829(3)
_cell_length_b                   10.3305(5)
_cell_length_c                   11.6459(6)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    93
_cell_measurement_theta_max      75.6140
_cell_measurement_theta_min      4.0140
_cell_volume                     887.21(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_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     58.00  92.00   0.50    0.12    --   47.66-135.00 -15.00   68
  2  \w     55.00 119.00   0.50    0.50    --  102.75-135.00 -15.00  128
  3  \w     41.00 110.00   0.50    0.50    --  102.75-125.00  90.00  138
  4  \w     82.00 116.00   0.50    0.50    --  102.75-134.00 164.00   68
  5  \w     25.00  96.00   0.50    0.12    --   47.66-134.00 164.00  142
  6  \w     58.00 102.00   0.50    0.50    --  102.75 -94.00-180.00   88
  7  \w     35.00  70.00   0.50    0.50    --  102.75 -61.00 -60.00   70
  8  \w     39.00  64.00   0.50    0.50    --  102.75 -61.00   0.00   50
  9  \w     36.00  71.00   0.50    0.50    --  102.75 -61.00-180.00   70
 10  \w     95.00 171.00   0.50    0.50    --  102.75  15.00-180.00  152
 11  \w     95.00 171.00   0.50    0.50    --  102.75  45.00-120.00  152
 12  \w    116.00 173.00   0.50    0.50    --  102.75  45.00 -90.00  114
 13  \w     62.00 118.00   0.50    0.12    --   47.66  77.00-150.00  112
 14  \w     35.00 117.00   0.50    0.12    --   47.66  57.00 -30.00  164
 15  \w     74.00 118.00   0.50    0.12    --   47.66 135.00  50.00   88
 16  \w     99.00 124.00   0.50    0.50    --  102.75 135.00  50.00   50
 17  \w    119.00 146.00   0.50    0.50    --  102.75 134.00-128.00   54
 18  \w    -66.00 -41.00   0.50    0.50    -- -102.75  61.00-150.00   50
 19  \w    -62.00 -37.00   0.50    0.50    -- -102.75  61.00-180.00   50
 20  \w    -87.00 -55.00   0.50    0.50    -- -102.75  77.00-180.00   64
 21  \w    -95.00 -32.00   0.50    0.50    -- -102.75  77.00-120.00  126
 22  \w    -56.00 -31.00   0.50    0.50    -- -102.75  61.00 -90.00   50
 23  \w    -22.00  26.00   0.50    0.12    --  -47.66  19.00-150.00   96
 24  \w    -23.00  24.00   0.50    0.12    --  -47.66  19.00 -90.00   94
 25  \w    -65.00 -31.00   0.50    0.50    -- -102.75  61.00   0.00   68
 26  \w    -80.00 -54.00   0.50    0.50    -- -102.75  77.00  30.00   52
 27  \w   -110.00 -35.00   0.50    0.50    -- -102.75 125.00 -30.00  150
 28  \w   -117.00 -36.00   0.50    0.50    -- -102.75 134.00-128.00  162
 29  \w    -66.00 -40.00   0.50    0.12    --  -47.66 134.00-128.00   52
 30  \w    -84.00 -58.00   0.50    0.12    --  -47.66 135.00  50.00   52
 31  \w   -119.00 -49.00   0.50    0.50    -- -102.75 135.00  50.00  140
 32  \w   -174.00 -96.00   0.50    0.50    -- -102.75 -15.00 150.00  156
 33  \w   -169.00 -93.00   0.50    0.50    -- -102.75 -45.00  60.00  152
 34  \w   -118.00 -79.00   0.50    0.12    --  -47.66-135.00 -15.00   78
 35  \w   -145.00-120.00   0.50    0.50    -- -102.75-135.00 -15.00   50
 36  \w   -111.00 -85.00   0.50    0.12    --  -47.66-134.00 164.00   52
 37  \w   -145.00-120.00   0.50    0.50    -- -102.75-134.00 164.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590449000
_diffrn_orient_matrix_UB_12      -0.0870313000
_diffrn_orient_matrix_UB_13      -0.1338284000
_diffrn_orient_matrix_UB_21      0.0259139000
_diffrn_orient_matrix_UB_22      0.1287211000
_diffrn_orient_matrix_UB_23      -0.0429233000
_diffrn_orient_matrix_UB_31      0.1916966000
_diffrn_orient_matrix_UB_32      -0.0164982000
_diffrn_orient_matrix_UB_33      -0.0006819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10421
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.321
_diffrn_reflns_theta_min         4.033
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.91a (Rigaku Oxford Diffraction, 2023)
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    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.119
_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     248
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0850
_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^)+(0.1894P)^2^+0.0987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2949
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04027b2.cif
_cod_data_source_block           hyd_BzIm
_cod_original_cell_volume        887.21(7)
_cod_database_code               7251711
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.636
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C18(H18A,H18B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_shelx_res_checksum              16903
_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 2.072
_oxdiff_exptl_absorpt_empirical_full_min 0.323