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_7251712
_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         'C46 H42 N4 O8, 2(C H4 O)'
_chemical_formula_sum            'C48 H50 N4 O10'
_chemical_formula_weight         842.92
_chemical_name_systematic
'Bisnaphthoimidazole-Based Hydrindacene Receptor'
_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             2025-07-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2025-09-22 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                111.251(5)
_cell_angle_beta                 101.585(5)
_cell_angle_gamma                94.648(5)
_cell_formula_units_Z            1
_cell_length_a                   7.6813(12)
_cell_length_b                   10.6712(17)
_cell_length_c                   14.613(2)
_cell_measurement_reflns_used    1158
_cell_measurement_temperature    90
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.98
_cell_volume                     1078.0(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      90
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9187
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.052
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.7210.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             446
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.1084
_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^)+(0.1145P)^2^+3.6765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2716
_refine_ls_wR_factor_ref         0.2945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2345
_reflns_number_total             3657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04027b2.cif
_cod_data_source_block           hyd_NpIm
_cod_database_code               7251712
_shelx_shelxl_version_number     2019/3
_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:
 C00H(H00A,H00B), C00M(H00C,H00D), C00O(H00E,H00F), C00U(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00G(H00G), C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00S(H00U,H00V,H00W), C00T(H00H,H00I,H00J), C00V(H00O,H00S,H00T)
2.d Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              16754
_olex2_submission_special_instructions 'No special instructions were received'