A sulfone-functionalized molecular triangle as a strong anion receptor driven by anion-π interactions.
Ma, Yifan; Song, Zihang; Guo, Sidan; Han, Han; Cai, Kang; Chemical communications (Cambridge, England) 61 (2025) 4531–4534; doi:10.1039/d4cc06077f

data_7134276
_publ_section_title
;
 A sulfone-functionalized molecular triangle as a strong anion receptor
 driven by anion-&#x3c0; interactions.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4531
_journal_page_last               4534
_journal_paper_doi               10.1039/d4cc06077f
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C2 H4 Cl2, C60 H60 N6 O24 S6, H2 O'
_chemical_formula_sum            'C62 H66 Cl2 N6 O25 S6'
_chemical_formula_weight         1558.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-19
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-02-05 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.576(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.5385(8)
_cell_length_b                   20.3950(10)
_cell_length_c                   17.6470(10)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      49.136
_cell_measurement_theta_min      2.721
_cell_volume                     5086.4(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.1013
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            66828
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        48.999
_diffrn_reflns_theta_max         48.999
_diffrn_reflns_theta_min         2.720
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.461
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1358 before and 0.0925 after correction.
The Ratio of minimum to maximum transmission is 0.5858.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.018
_exptl_crystal_description       block
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.254(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     916
_refine_ls_number_reflns         15065
_refine_ls_number_restraints     388
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1120P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                10084
_reflns_number_total             15065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06077f2.cif
_cod_data_source_block           240412myf
_cod_depositor_comments
'Adding full bibliography for 7134275--7134276.cif.'
_cod_database_code               7134276
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.789
_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, All O(H,H) groups
2. Restrained distances
 C9-C10 = C21-C20
 1.53 with sigma of 0.01
 C2-C1
 1.53 with sigma of 0.01
 C4-C5
 1.54 with sigma of 0.02
 C17-C18
 1.54 with sigma of 0.02
 C5-C4
 1.54 with sigma of 0.002
 C40-C41
 1.54 with sigma of 0.002
 Cl1-C1 \\sim Cl2-C2
 with sigma of 0.02
3. Rigid bond restraints
 C16, C57, C58, C59, C60, C15
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 S4, O14, S4, C26, O7, C12, O12, C23, N1, C5, N4, C23, N4, C24, C3, C4, C8,
 C11, C19, C22, C61, C62
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C54, C55, O13, C24
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O1, S1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, O2, C3, S1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O4, C6
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O8, C13
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 N6, C39
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C14, C11, C8, C7, C4, C3
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C10, C9
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C34, C45, C35, C38, C41, C42
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C47, C52, C51, C50, C49, C48
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O6, S2, O5
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C24, O13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O10, S3, O11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C24, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S5, C36, O19, O18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C25, C26, C29, C18, C19, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C46, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
S6 \\sim C43 \\sim C44 \\sim O23 \\sim O22 \\sim C42: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
C54 \\sim C55 \\sim C56 \\sim C31 \\sim C32 \\sim C53: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
C9 \\sim C10: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C1 \\sim C2 \\sim Cl1 \\sim Cl2: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
C47 \\sim C52 \\sim C51 \\sim C50 \\sim C49 \\sim C48: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C27 \\sim C28: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C10 \\sim C9 \\sim S2: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C16 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C15: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
O5 \\sim S2 \\sim O6: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
C61 \\sim C62 \\sim S1: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
C24 \\sim C25: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C22 \\sim C19 \\sim C18 \\sim C29 \\sim C26 \\sim C25: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C55) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O5) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 S1, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, O2, C3, S1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed X: S1(0.329121)
 Fixed Y: S1(-0.212591)
 Fixed Z: S1(0.431729)
7.a Free rotating group:
 O25(H25A,H25B)
7.b Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C31(H31), C32(H32), C47(H47), C48(H48)
7.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C9(H9A,H9B), C20(H20A,H20B), C27(H27A,H27B),
 C36(H36A,H36B), C43(H43A,H43B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
  C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,
 H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
 C61(H61A,H61B)
7.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C37(H37A,H37B,
 H37C), C44(H44A,H44B,H44C), C62(H62A,H62B,H62C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4952
_shelx_hkl_checksum              97756
_shelx_fab_checksum              45131
_olex2_submission_special_instructions 'No special instructions were received'