<i>N</i>-Arylsulfonamidocalix[4]arenes with narrow pH-responsive binding near neutral pH.
Alarcon-Miranda, Carlos; Middleton, Isis A.; Rusli, Olivia; Caceres-Herrera, Nicolas; Bhadbhade, Mohan; Rijs, Nicole J.; Thordarson, Pall; Kogan, Marcelo J.; Saitz, Claudio; Chemical science 17 (2026) 3293–3299; doi:10.1039/d5sc07965a

data_1576469
_publ_section_title
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 <i>N</i>-Arylsulfonamidocalix[4]arenes with narrow pH-responsive binding
 near neutral pH.
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_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              3293
_journal_page_last               3299
_journal_paper_doi               10.1039/d5sc07965a
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C64 H68 N4 O16 S4, 2(H2 O)'
_chemical_formula_sum            'C64 H72 N4 O18 S4'
_chemical_formula_weight         1313.49
_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
_audit_creation_date             2024-10-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-04 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.032(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9582(11)
_cell_length_b                   15.4314(9)
_cell_length_c                   20.0065(9)
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      2.36
_cell_volume                     6408.5(6)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            265339
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.129
_diffrn_reflns_theta_max         25.129
_diffrn_reflns_theta_min         2.134
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1162 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.9020.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.039
_refine_diff_density_max         1.573
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     861
_refine_ls_number_reflns         11393
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0451P)^2^+18.1532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9572
_reflns_number_total             11393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07965a2.cif
_cod_data_source_block           carlos_calixn_a
_cod_database_code               1576469
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.923
_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. Restrained distances
 C1DD-C2DD \\sim C1DD-C2D'
 with sigma of 0.02
 O2DD-C2DD \\sim O2DD-C2D'
 with sigma of 0.02
 C2DD-O2D' \\sim C2D'-O2D'
 with sigma of 0.02
 C2D'-C1DD \\sim C2DD-C1DD
 with sigma of 0.02
 O2DD-C2DD \\sim O2D'-C2D'
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O2D', C2D', O2DD, C2DD
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O2D'(0.4) C2D'(0.4) H2DA(0.4) H2DB(0.4) C3D'(0.4) H3DA(0.4)
 H3DB(0.4) H3DC(0.4) O2DD(0.6) C2DD(0.6) H2DC(0.6) H2DD(0.6) C3DD(0.6)
 H3DD(0.6) H3DE(0.6) H3DF(0.6)
5.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
5.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C1BB(H1BA,H1BB), C1CC(H1CA,H1CB), C1DD(H1DA,H1DB), C1M(H1MA,
 H1MB), C2AA(H2AA,H2AB), C2BB(H2BA,H2BB), C2CC(H2CA,H2CB), C2M(H2MA,H2MB),
 C3M(H3MA,H3MB), C4M(H4MA,H4MB), C2D'(H2DA,H2DB), C2DD(H2DC,H2DD)
5.c Aromatic/amide H refined with riding coordinates:
 N1B(H1B), C2A(H2A), C2B(H2B), C2C(H2C), C2D(H2D), C6A(H6A), C6B(H6B),
 C6C(H6C), C6D(H6D), C8A(H8A), C8B(H8B), C8C(H8C), C8D(H8D), C9A(H9A), C9B(H9B),
  C9C(H9C), C9D(H9D), C10A(H10A), C10B(H10B), C10C(H10C), C10D(H10D),
 C11A(H11A), C11B(H11B), C11C(H11C), C11D(H11D), C12A(H12A), C12B(H12B),
 C12C(H12C), C12D(H12D)
5.d Idealised Me refined as rotating group:
 C3AA(H3AA,H3AB,H3AC), C3BB(H3BA,H3BB,H3BC), C3CC(H3CA,H3CB,H3CC), C3D'(H3DA,
 H3DB,H3DC), C3DD(H3DD,H3DE,H3DF)
;
_shelx_res_checksum              6074
_shelx_hkl_checksum              65183
_olex2_submission_special_instructions 'No special instructions were received'