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_7160300
_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         'C49 H44 Cs F4 N4 O, F'
_chemical_formula_sum            'C49 H44 Cs F5 N4 O'
_chemical_formula_weight         932.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-06-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-27 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6024(3)
_cell_length_b                   17.3934(5)
_cell_length_c                   12.9275(4)
_cell_measurement_reflns_used    8704
_cell_measurement_temperature    281(2)
_cell_measurement_theta_max      20.22
_cell_measurement_theta_min      2.42
_cell_volume                     2158.24(11)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.999
_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  0.1018
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            39435
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.366
_diffrn_reflns_theta_min         2.122
_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    0.921
_exptl_absorpt_correction_T_max  0.5619
_exptl_absorpt_correction_T_min  0.5149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.9164.
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    1.435
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0722
_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^)+(0.0615P)^2^+4.7449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             4105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01708k2.cif
_cod_data_source_block           final2_a
_cod_depositor_comments
'Adding full bibliography for 7160298--7160301.cif.'
_cod_database_code               7160300
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, H24 of C24, H15 of C15, H6 of C6, H3 of C3, H7 of C7, H18
  of C18, H11 of C11, H12 of C12, H25 of C25, H2A of C2, H14 of C14, H19 of C19
 At 1.5 times of:
  All C(H,H,H) groups, H30B of C30, All O(H) groups
2. Others
 Fixed Sof: H21A(0.5) H21B(0.5) H21C(0.5) H29A(0.5) H29B(0.5) H29C(0.5)
3.a Ternary CH refined with riding coordinates:
 N1(H1A), N2(H2)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              47500
_olex2_submission_special_instructions 'No special instructions were received'