Submicromolar fluorescence 'turn-on' detection of fluoride anions using <i>meso</i>-(tetra-aryl) calix[4]pyrrole.
Roy, Anik; Dutta, Ranjan; Halder, Dibakar; Mandal, Koushik; Kundu, Somenath; Hossain, Maidul; Saha, Indrajit; Lee, Chang-Hee; Organic & biomolecular chemistry 23 (2025) 1209–1214; doi:10.1039/d4ob01708k

data_7160299
_publ_section_title
;
 Submicromolar fluorescence 'turn-on' detection of fluoride anions using
 <i>meso</i>-(tetra-aryl) calix[4]pyrrole.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1209
_journal_page_last               1214
_journal_paper_doi               10.1039/d4ob01708k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C48 H40 F4 N4, C6 H14 N, F, 2(C H3) '
_chemical_formula_sum            'C56 H60 F5 N5'
_chemical_formula_weight         898.09
_space_group_crystal_system      tetragonal
_space_group_IT_number           130
_space_group_name_Hall           '-P 4a 2ac'
_space_group_name_H-M_alt        'P 4/n c c :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-09-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-09-27 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5418(6)
_cell_length_b                   15.5418(6)
_cell_length_c                   19.8506(11)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    281(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.43
_cell_volume                     4794.9(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      281.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            62658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         2.435
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0710 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.324
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.1280
_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^)+(0.0675P)^2^+17.5128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2655
_refine_ls_wR_factor_ref         0.2732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1907
_reflns_number_total             2204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01708k2.cif
_cod_data_source_block           final2_c
_cod_depositor_comments
'Adding full bibliography for 7160298--7160301.cif.'
_cod_original_cell_volume        4794.9(5)
_cod_original_sg_symbol_H-M      'P 4/n c c'
_cod_database_code               7160299
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
N1 \\sim C2 \\sim C3 \\sim C2A \\sim C3A: within 2A with sigma of 0.002 and
sigma for terminal atoms of 0.004 within 2A
N2 \\sim C4 \\sim C5 \\sim C6 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12
\\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim F2 \\sim F1: within 2A with sigma
of 0.002 and sigma for terminal atoms of 0.004 within 2A
2. Others
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C2A(0.5) H2AC(0.5) H2AB(0.5) H2AA(0.5) C3A(0.5) H3AA(0.5) H3AB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3A(H3AA,H3AB)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C12(H12B,H12A,H12C), C2(H2A,H2B,H2C), C2A(H2AC,H2AB,H2AA)
;
_shelx_res_checksum              75476
_olex2_submission_special_instructions 'No special instructions were received'