A calix[4]pyrrole functionalized with an amidoindole ester for the selective recognition of the dihydrogen phosphate anion.
Oh, Ju Hyun; Shin, Sang Kyu; Kim, Sung Kuk; Chemical communications (Cambridge, England) 61 (2025) 13425–13428; doi:10.1039/d5cc03617h

data_7134877
_publ_section_title
;
 A calix[4]pyrrole functionalized with an amidoindole ester for the
 selective recognition of the dihydrogen phosphate anion.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13425
_journal_page_last               13428
_journal_paper_doi               10.1039/d5cc03617h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C54 H60 N8 O6, C16 H36 N, H2 O4 P'
_chemical_formula_sum            'C70 H98 N9 O10 P'
_chemical_formula_weight         1256.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-27
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.228(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0616(2)
_cell_length_b                   16.1110(2)
_cell_length_c                   32.0350(5)
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.0650
_cell_measurement_theta_min      1.7570
_cell_volume                     7214.58(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'SHELXTL-Plus, Bruker AXS, Inc. 2009'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.682
_diffrn_measured_fraction_theta_max 0.682
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -180.00 -60.00   0.50    2.00   0.00   0.00   0.00    --   240
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0361164000
_diffrn_orient_matrix_UB_12      0.0515367000
_diffrn_orient_matrix_UB_13      0.0015389000
_diffrn_orient_matrix_UB_21      0.0172111000
_diffrn_orient_matrix_UB_22      0.0160457000
_diffrn_orient_matrix_UB_23      -0.0276320000
_diffrn_orient_matrix_UB_31      -0.0573663000
_diffrn_orient_matrix_UB_32      -0.0276154000
_diffrn_orient_matrix_UB_33      -0.0132886000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.97741
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.682
_diffrn_reflns_Laue_measured_fraction_max 0.682
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6768
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        26.503
_diffrn_reflns_theta_max         26.503
_diffrn_reflns_theta_min         1.948
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       plank
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_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     831
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     540
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0513
_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^)+(0.1002P)^2^+6.8843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3521
_reflns_number_total             3926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03617h2.cif
_cod_data_source_block           oh-2
_cod_depositor_comments          'Adding full bibliography for 7134877.cif.'
_cod_database_code               7134877
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C48H32N4O4
_reflns_odcompleteness_completeness 67.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.50
_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,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C39(H39A,H39B), C50(H50A,H50B), C53(H53A,H53B), C55(H55A,
 H55B), C56(H56A,H56B), C57(H57A,H57B), C59(H59A,H59B), C60(H60A,H60B),
 C61(H61A,H61B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C67(H67A,H67B),
  C68(H68A,H68B), C69(H69A,H69B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), N7(H7), N8(H8), C2(H2A),
 C3(H3A), C7(H7A), C8(H8A), C12(H12), C13(H13), C17(H17), C18(H18), C31(H31),
 C32(H32), C33(H33), C45(H45), C46(H46), C47(H47)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C37(H37A,H37B,H37C), C40(H40A,
 H40B,H40C), C51(H51A,H51B,H51C), C54(H54A,H54B,H54C), C58(H58A,H58B,H58C),
 C62(H62A,H62B,H62C), C66(H66A,H66B,H66C), C70(H70A,H70B,H70C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52851
_shelx_hkl_checksum              62578
_shelx_fab_checksum              82536
_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 2.490
_oxdiff_exptl_absorpt_empirical_full_min 0.455