Selective recognition and sensing of biologically important phosphates using triptycene-based anion receptors.
Kassir, Ahmad F.; Lupp, Daniel; Grabowski, Jakub; Granda, Jarosław M; Jurczak, Janusz; Organic & biomolecular chemistry 23 (2025) 6969–6977; doi:10.1039/d5ob00760g

data_7160628
_publ_section_title
;
 Selective recognition and sensing of biologically important phosphates
 using triptycene-based anion receptors.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6969
_journal_page_last               6977
_journal_paper_doi               10.1039/d5ob00760g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety
'2(C28 H26 N2 O2), C27.2 H24 N2 O2, 0.5(C2 H5), C27.8 H25.5 N2 O2, 2(C2 H6 O S), 1.2(O)'
_chemical_formula_sum            'C116 H116 N8 O11.2 S2'
_chemical_formula_weight         1865.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                80.044(2)
_cell_angle_beta                 79.078(2)
_cell_angle_gamma                71.2037(19)
_cell_formula_units_Z            2
_cell_length_a                   15.7796(14)
_cell_length_b                   16.5721(15)
_cell_length_c                   20.6662(18)
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.28
_cell_volume                     4986.9(8)
_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      100.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            72833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.272
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       prism
_exptl_crystal_F_000             1979
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1391
_refine_ls_number_reflns         18001
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0580P)^2^+2.4683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13563
_reflns_number_total             18001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00760g2.cif
_cod_data_source_block           jga_260_2
_cod_depositor_comments
'Adding full bibliography for 7160628--7160629.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C116 H116 N8 O11.20 S2'
_cod_database_code               7160628
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C27C, C27E}
{C27F, C27H}
3. Restrained distances
 C25G-C26G = C26G-C27G = C27G-C28G
 1.5 with sigma of 0.02
 N2G-C26G = C25G-C27G = C26G-C28G
 2.53 with sigma of 0.04
 C27F-C28F = C27H-C28H
 1.5 with sigma of 0.03
4. Uiso/Uaniso restraints and constraints
Uanis(C28E) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C27C) = Uanis(C27E)
Uanis(C27F) = Uanis(C27H)
5. Others
 Fixed Sof: N2C(0.9) C25C(0.9) H25A(0.9) H25B(0.9) C26C(0.9) H26A(0.9)
 H26B(0.9) C27C(0.5) H27A(0.5) H27B(0.5) C28C(0.5) H28A(0.5) H28B(0.5)
 H28C(0.5) C27E(0.4) H27M(0.4) H27N(0.4) C28E(0.4) H28S(0.4) H28T(0.4)
 H28U(0.4) N2G(0.1) C25G(0.1) H25C(0.1) H25D(0.1) C26G(0.1) H26C(0.1) H26D(0.1)
 C27G(0.1) H27C(0.1) H27D(0.1) C28G(0.1) H28D(0.1) H28E(0.1) H28F(0.1)
 C25D(0.5) H25E(0.5) H25F(0.5) C26D(0.5) H26E(0.5) H26F(0.5) C27D(0.5)
 H27E(0.5) H27F(0.5) C28D(0.5) H28G(0.5) H28H(0.5) H28I(0.5) C25F(0.5)
 H25G(0.5) H25H(0.5) C26F(0.5) H26G(0.5) H26H(0.5) C27F(0.4) H27G(0.4)
 H27H(0.4) C28F(0.4) H28J(0.4) H28K(0.4) H28L(0.4) C27H(0.1) H27O(0.1)
 H27P(0.1) C28H(0.1) H28V(0.1) H28W(0.1) H28X(0.1) S1X1(0.9) O1X1(0.9)
 C1X1(0.9) H1XA(0.9) H1XB(0.9) H1XC(0.9) C2X1(0.9) H2XA(0.9) H2XB(0.9)
 H2XC(0.9) S1X2(0.1) O1X2(0.1) C1X2(0.1) H1XD(0.1) H1XE(0.1) H1XF(0.1)
 C2X2(0.1) H2XD(0.1) H2XE(0.1) H2XF(0.1) S1Y(0.8) O1Y(0.8) C1Y(0.8) H1YA(0.8)
 H1YB(0.8) H1YC(0.8) C2Y(0.8) H2YA(0.8) H2YB(0.8) H2YC(0.8) S1Y2(0.2) O1Y2(0.2)
 C1Y2(0.2) H1YD(0.2) H1YE(0.2) H1YF(0.2) C2Y2(0.2) H2YD(0.2) H2YE(0.2)
 H2YF(0.2) O1W1(0.8) O1W2(0.4)
6.a Riding coordinates:
 C27E(H27M,H27N), C27H(H27O,H27P)
6.b Ternary CH refined with riding coordinates:
 C1A(H1AA), C8A(H8A), C1B(H1BA), C8B(H8B), C1C(H1CA), C8C(H8C), C1D(H1DA),
 C8D(H8D)
6.c Secondary CH2 refined with riding coordinates:
 C25A(H25I,H25J), C26A(H26I,H26J), C27A(H27I,H27J), C25B(H25K,H25L), C26B(H26K,
 H26L), C27B(H27K,H27L), C25C(H25A,H25B), C26C(H26A,H26B), C27C(H27A,H27B),
 C25G(H25C,H25D), C26G(H26C,H26D), C27G(H27C,H27D), C25D(H25E,H25F), C26D(H26E,
 H26F), C27D(H27E,H27F), C25F(H25G,H25H), C26F(H26G,H26H), C27F(H27G,H27H)
6.d Me refined with riding coordinates:
 C28G(H28D,H28E,H28F), C1X2(H1XD,H1XE,H1XF), C2X2(H2XD,H2XE,H2XF), C1Y2(H1YD,
 H1YE,H1YF), C2Y2(H2YD,H2YE,H2YF)
6.e Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C19A(H19A), C22A(H22A), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B),
 C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C19B(H19B), C22B(H22B),
 C3C(H3C), C4C(H4C), C5C(H5C), C6C(H6C), C10C(H10C), C11C(H11C), C12C(H12C),
 C13C(H13C), C19C(H19C), C22C(H22C), C3D(H3D), C4D(H4D), C5D(H5D), C6D(H6D),
 C10D(H10D), C11D(H11D), C12D(H12D), C13D(H13D), C19D(H19D), C22D(H22D)
6.f Idealised Me refined as rotating group:
 C21A(H21G,H21H,H21I), C28A(H28M,H28N,H28O), C21B(H21J,H21K,H21L), C28B(H28P,
 H28Q,H28R), C21C(H21A,H21B,H21C), C28C(H28A,H28B,H28C), C28E(H28S,H28T,H28U),
 C21D(H21D,H21E,H21F), C28D(H28G,H28H,H28I), C28F(H28J,H28K,H28L), C28H(H28V,
 H28W,H28X), C1X1(H1XA,H1XB,H1XC), C2X1(H2XA,H2XB,H2XC), C1Y(H1YA,H1YB,H1YC),
 C2Y(H2YA,H2YB,H2YC)
;
_shelx_res_checksum              5863
_olex2_submission_special_instructions 'No special instructions were received'