<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_1576470
_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
'C68 H64 F12 N4 Na O24 S8, 0.375(C2 H8 O2), 2[Na2]'
_chemical_formula_sum            'C68.75 H67 F12 N4 Na5 O24.75 S8'
_chemical_formula_weight         1944.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-08-08
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-08 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.284(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.840(3)
_cell_length_b                   19.926(2)
_cell_length_c                   22.459(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      23.146
_cell_measurement_theta_min      2.449
_cell_volume                     9204(2)
_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      120.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2582
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            154779
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        23.513
_diffrn_reflns_theta_max         23.513
_diffrn_reflns_theta_min         1.980
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.3723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1664 before and 0.1156 after correction.
The Ratio of minimum to maximum transmission is 0.4998.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       needle
_exptl_crystal_F_000             3986
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.383
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         6722
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.1208
_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^)+(0.0974P)^2^+153.3958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2692
_refine_ls_wR_factor_ref         0.2836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5246
_reflns_number_total             6722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07965a2.cif
_cod_data_source_block           carlos_tetrana_c_pl
_cod_database_code               1576470
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3BA,H3BB,H3BC} of C3BB, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, {H3AA,H3AB,H3AC} of C3AA, {H2D,H2E,H2C} of C2
2. Restrained distances
 O00R-C1BC = O00R-C1BB
 1.38 with sigma of 0.02
 C2BC-C1BB = C2BB-C1BC
 1.51 with sigma of 0.02
 S1-C7
 1.8 with sigma of 0.02
 F4A-C7 = F2-C7 = F4-C1 = F1A-C1 = F2A-C1
 1.31 with sigma of 0.02
 S1-F4A
 2.58 with sigma of 0.02
 F2A-S1
 2.58 with sigma of 0.02
 F1A-S1
 2.58 with sigma of 0.02
 F2-S1
 2.58 with sigma of 0.02
 O2A-H2E
 2.006 with sigma of 0.01
 O00F-C2BB \\sim O00F-C2BC
 with sigma of 0.02
 F2-C7 \\sim F4-C7
 with sigma of 0.02
 F2-C7 \\sim F2A-C7
 with sigma of 0.02
 F4-C7 \\sim F4A-C7
 with sigma of 0.02
 S1-C7 \\sim S1-C1
 with sigma of 0.02
 F2-C7 \\sim F2-C1
 with sigma of 0.02
 F4-C7 \\sim F4-C1
 with sigma of 0.02
 C7-F4A \\sim C1-F4A
 with sigma of 0.02
 C7-F1A \\sim C1-F1A
 with sigma of 0.02
 C7-F2A \\sim C1-F2A
 with sigma of 0.02
 C7-F2 \\sim C7-F4A
 with sigma of 0.02
 C1-F1A \\sim C1-F4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2BC) = Uanis(C1BB)
Uanis(C2BB) = Uanis(C1BC)
Uanis(C7A) = Uanis(N1A)
Uanis(C7) = Uanis(C1)
Uanis(C1M) = Uanis(C2B)
4. Rigid body (RIGU) restrains
 C2BC, C2BB, C1BC, C1BB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, F2, F4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F4, C7, F4A, F1A, F2A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C1BB(0.5) H1BA(0.5) H1BB(0.5) C2BB(0.5) H2BA(0.5) H2BB(0.5)
 C2BC(0.5) H2BC(0.5) H2BD(0.5) C1BC(0.5) H1BC(0.5) H1BD(0.5) F2(0.5) F4(0.5)
 C7(0.5) F4A(0.5) F2A(0.5) C1(0.5) C2(0.375) H2D(0.375) H2E(0.375) H2C(0.375)
 O3(0.375) H3(0.375)
6.a Riding coordinates:
 N1A(H1A), N1B(H1B), C3BB(H3BA,H3BB,H3BC), C6B(H6B)
6.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C1BB(H1BA,H1BB), C1M(H1MA,H1MB), C2AA(H2AA,H2AB), C2BB(H2BA,
 H2BB), C2M(H2MA,H2MB), C2BC(H2BC,H2BD), C1BC(H1BC,H1BD)
6.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C6A(H6A), C8A(H8A), C8B(H8B), C9A(H9A), C9B(H9B),
 C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B)
6.d Idealised Me refined as rotating group:
 C3AA(H3AA,H3AB,H3AC), C2(H2D,H2E,H2C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
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_smtbx_masks_special_details
;
A solvent mask was calculated and 492 electrons were 
found in a volume of 1738\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
2[Na2] per Asymmetric Unit 
which account for 176 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              87762
_shelx_hkl_checksum              63749
_shelx_fab_checksum              95404
_olex2_submission_special_instructions 'No special instructions were received'