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_7134275
_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 rmad
_chemical_formula_moiety         'C76 H96 N7 O24 S6, Cl O4'
_chemical_formula_sum            'C76 H96 Cl N7 O28 S6'
_chemical_formula_weight         1783.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.100(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.2633(5)
_cell_length_b                   16.5145(6)
_cell_length_c                   17.4282(6)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.455
_cell_measurement_theta_min      3.349
_cell_volume                     4393.0(3)
_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      170.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40157
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.937
_diffrn_reflns_theta_min         2.518
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1571 before and 0.0762 after correction.
The Ratio of minimum to maximum transmission is 0.7034.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             1876
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 3704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.101(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1294
_refine_ls_number_reflns         16291
_refine_ls_number_restraints     1005
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.1043
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2838
_refine_ls_wR_factor_ref         0.3174
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                10512
_reflns_number_total             16291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06077f2.cif
_cod_data_source_block           240723ck_myf_cl
_cod_depositor_comments
'Adding full bibliography for 7134275--7134276.cif.'
_cod_database_code               7134275
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.776
_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. Restrained distances
 Cl3-O1A = Cl3-O1B = Cl3-O1C = Cl3-O1D
 1.5 with sigma of 0.02
 C59-C1P
 2.8 with sigma of 0.01
 Cl1-O3 = Cl1-O1 = Cl1-O2 = Cl1-O1E
 1.5 with sigma of 0.02
 N8-C1A = N8-C1B = N8-C1C = N8-C1D = C1A-C1E = C1B-C1F = C1C-C1G = C1D-C1H =
 C1E-C1I
 1.52 with sigma of 0.02
 C1F-C1J = C1G-C1K = C1H-C1L
 1.53 with sigma of 0.02
 C1I-C1M = C1J-C1N = C1K-C1O = C1L-C1P
 1.49 with sigma of 0.02
 O12-C1L_$1
 2.4 with sigma of 0.01
 S3-C22
 1.7 with sigma of 0.01
 C1B-C1A
 2.44 with sigma of 0.01
 C1H-C1A
 2.44 with sigma of 0.01
 N9-C2G = N9-C2H = N9-C2I = N9-C2J = C2G-C2K = C2H-C2L = C2I-C2M = C2J-C2N =
 C2K-C2O
 1.52 with sigma of 0.02
 C2L-C2P = C2M-C2Q = C2N-C2R
 1.53 with sigma of 0.02
 C2O-C2S = C2P-C2T = C2Q-C2U = C2R-C2V
 1.49 with sigma of 0.02
 O23-C2U
 2.5 with sigma of 0.01
 C56-C2P
 2.5 with sigma of 0.01
 O14-C2R
 2.5 with sigma of 0.01
 C2J-C2H
 2.44 with sigma of 0.01
 C2N-C2K
 2.44 with sigma of 0.01
 S6-C52
 1.7 with sigma of 0.01
 C53-C52
 1.53 with sigma of 0.01
 O29_$2-C2S
 2.5 with sigma of 0.01
 C1G-C1D
 2.45 with sigma of 0.01
 C56-C2L
 2.5 with sigma of 0.01
 C2H-C56
 2.8 with sigma of 0.01
 C2H-C2M
 2.5 with sigma of 0.01
 C2L-C56
 2.8 with sigma of 0.01
 C1L-C1A
 2.6 with sigma of 0.01
 C2I-C2G
 2.4 with sigma of 0.01
 N8-C1E = N8-C1G
 2.56 with sigma of 0.04
 N8-C1F = N8-C1H
 2.59 with sigma of 0.04
 C1A-C1I = C1B-C1J = C1C-C1K = C1D-C1L
 2.48 with sigma of 0.04
 C1E-C1M = C1F-C1N = C1G-C1O = C1H-C1P
 2.53 with sigma of 0.04
 N9-C2K = N9-C2M
 2.56 with sigma of 0.04
 N9-C2L = N9-C2N
 2.59 with sigma of 0.04
 C2G-C2O = C2H-C2P = C2I-C2Q = C2J-C2R
 2.48 with sigma of 0.04
 C2K-C2S = C2L-C2T = C2M-C2U = C2N-C2V
 2.53 with sigma of 0.04
 S4-C59 \\sim S4-C59A
 with sigma of 0.02
 C59-C60 \\sim C59A-C60A
 with sigma of 0.02
 S4-C60 \\sim S4-C60A
 with sigma of 0.04
 Cl3-O1A \\sim Cl3-O1B \\sim Cl3-O1C \\sim Cl3-O1D
 with sigma of 0.02
 O1A-O1C \\sim O1B-O1D \\sim O1A-O1D \\sim O1B-O1C \\sim O1A-O1B \\sim O1C-O1D
 with sigma of 0.04
 Cl1-O3 \\sim Cl1-O1 \\sim Cl1-O2 \\sim Cl1-O1E
 with sigma of 0.02
 O3-O2 \\sim O1-O1E \\sim O3-O1E \\sim O1-O2 \\sim O3-O1 \\sim O2-O1E
 with sigma of 0.04
 N8-C1A \\sim N8-C1B \\sim N8-C1C \\sim N8-C1D
 with sigma of 0.02
 C1A-C1E \\sim C1E-C1I \\sim C1I-C1M \\sim C1D-C1H \\sim C1H-C1L \\sim C1L-C1P
\\sim C1C-C1G \\sim C1G-C1K
 \\sim C1K-C1O \\sim C1B-C1F \\sim C1F-C1J \\sim C1J-C1N
 with sigma of 0.02
 C1A-C1I \\sim C1E-C1M \\sim C1D-C1L \\sim C1H-C1P \\sim C1C-C1K \\sim C1G-C1O
\\sim C1B-C1J \\sim C1F-C1N
 with sigma of 0.04
 C1A-C1D \\sim C1D-C1C \\sim C1C-C1B
 with sigma of 0.04
 N9-C2G \\sim N9-C2H \\sim N9-C2I \\sim N9-C2J
 with sigma of 0.02
 C2G-C2K \\sim C2K-C2O \\sim C2O-C2S \\sim C2J-C2N \\sim C2N-C2R \\sim C2R-C2V
\\sim C2I-C2M \\sim C2M-C2Q
 \\sim C2Q-C2U \\sim C2H-C2L \\sim C2L-C2P \\sim C2P-C2T
 with sigma of 0.02
 C2G-C2O \\sim C2K-C2S \\sim C2J-C2R \\sim C2N-C2V \\sim C2I-C2Q \\sim C2M-C2U
\\sim C2H-C2P \\sim C2L-C2T
 with sigma of 0.04
 C2G-C2J \\sim C2J-C2I \\sim C2I-C2H
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C59A \\sim C59 \\sim C60 \\sim C60A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Cl3 \\sim O1A \\sim O1B \\sim O1C \\sim O1D: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Cl1 \\sim O3 \\sim O1 \\sim O2 \\sim O1E: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
N8 \\sim C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F \\sim C1G \\sim
C1H \\sim C1I \\sim C1J \\sim C1K \\sim C1L \\sim C1M \\sim C1N \\sim C1O \\sim
C1P: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within
2A
C22 \\sim C23 \\sim S3: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
S6 \\sim C52 \\sim C53: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
N9 \\sim C2G \\sim C2H \\sim C2I \\sim C2J \\sim C2K \\sim C2L \\sim C2M \\sim
C2N \\sim C2O \\sim C2P \\sim C2Q \\sim C2R \\sim C2S \\sim C2T \\sim C2U \\sim
C2V: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C2H \\sim C2L: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C2L \\sim C2H \\sim C2P: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C2N) \\sim Ueq, Uanis(C2R) \\sim Ueq, Uanis(C2J) \\sim Ueq, Uanis(N9)
\\sim Ueq, Uanis(C2I) \\sim Ueq, Uanis(C2M) \\sim Ueq, Uanis(C2Q) \\sim Ueq,
Uanis(C2U) \\sim Ueq, Uanis(C2G) \\sim Ueq, Uanis(C2H) \\sim Ueq, Uanis(C2K)
\\sim Ueq, Uanis(C2O) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(C2T) \\sim Ueq,
Uanis(C2P) \\sim Ueq, Uanis(C2L) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1C) \\sim Ueq, Uanis(C1G) \\sim Ueq, Uanis(C1K) \\sim Ueq, Uanis(C1O)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Cl3, O1A, O1B, O1C, O1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1, O3, O1, O2, O1E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N8, C1A, C1B, C1C, C1D, C1E, C1F, C1G, C1H, C1I, C1J, C1K, C1L, C1M, C1N, C1O,
  C1P
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N9, C2G, C2H, C2I, C2J, C2K, C2L, C2M, C2N, C2O, C2P, C2Q, C2R, C2S, C2T, C2U,
  C2V
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C59(0.05) H59A(0.05) H59B(0.05) C60(0.05) H60A(0.05) H60B(0.05)
 H60C(0.05) Cl3(0.5) O1A(0.5) O1B(0.5) O1C(0.5) O1D(0.5) Cl1(0.5) O3(0.5)
 O1(0.5) O2(0.5) O1E(0.5) N8(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) C1B(0.5)
 H1BA(0.5) H1BB(0.5) C1C(0.5) H1CA(0.5) H1CB(0.5) C1D(0.5) H1DA(0.5) H1DB(0.5)
 C1E(0.5) H1EA(0.5) H1EB(0.5) C1F(0.5) H1FA(0.5) H1FB(0.5) C1G(0.5) H1GA(0.5)
 H1GB(0.5) C1H(0.5) H1HA(0.5) H1HB(0.5) C1I(0.5) H1IA(0.5) H1IB(0.5) C1J(0.5)
 H1JA(0.5) H1JB(0.5) C1K(0.5) H1KA(0.5) H1KB(0.5) C1L(0.5) H1LA(0.5) H1LB(0.5)
 C1M(0.5) H1MA(0.5) H1MB(0.5) H1MC(0.5) C1N(0.5) H1NA(0.5) H1NB(0.5) H1NC(0.5)
 C1O(0.5) H1OA(0.5) H1OB(0.5) H1OC(0.5) C1P(0.5) H1PA(0.5) H1PB(0.5) H1PC(0.5)
 N9(0.5) C2G(0.5) H2GA(0.5) H2GB(0.5) C2H(0.5) H2HA(0.5) H2HB(0.5) C2I(0.5)
 H2IA(0.5) H2IB(0.5) C2J(0.5) H2JA(0.5) H2JB(0.5) C2K(0.5) H2KA(0.5) H2KB(0.5)
 C2L(0.5) H2LA(0.5) H2LB(0.5) C2M(0.5) H2MA(0.5) H2MB(0.5) C2N(0.5) H2NA(0.5)
 H2NB(0.5) C2O(0.5) H2OA(0.5) H2OB(0.5) C2P(0.5) H2PA(0.5) H2PB(0.5) C2Q(0.5)
 H2QA(0.5) H2QB(0.5) C2R(0.5) H2RA(0.5) H2RB(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5)
 H2SC(0.5) C2T(0.5) H2TA(0.5) H2TB(0.5) H2TC(0.5) C2U(0.5) H2UA(0.5) H2UB(0.5)
 H2UC(0.5) C2V(0.5) H2VA(0.5) H2VB(0.5) H2VC(0.5) C59A(0.95) H59C(0.95)
 H59D(0.95) C60A(0.95) H60D(0.95) H60E(0.95) H60F(0.95)
6.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C17(H17), C43(H43), C46(H46), C47(H47)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C22(H22A,H22B), C25(H25A,H25B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C37(H37A,H37B),
  C44(H44A,H44B), C45(H45A,H45B), C52(H52A,H52B), C55(H55A,H55B), C56(H56A,
 H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C1A(H1AA,H1AB),
 C1B(H1BA,H1BB), C1C(H1CA,H1CB), C1D(H1DA,H1DB), C1E(H1EA,H1EB), C1F(H1FA,H1FB),
  C1G(H1GA,H1GB), C1H(H1HA,H1HB), C1I(H1IA,H1IB), C1J(H1JA,H1JB), C1K(H1KA,
 H1KB), C1L(H1LA,H1LB), C2G(H2GA,H2GB), C2H(H2HA,H2HB), C2I(H2IA,H2IB),
 C2J(H2JA,H2JB), C2K(H2KA,H2KB), C2L(H2LA,H2LB), C2M(H2MA,H2MB), C2N(H2NA,H2NB),
  C2O(H2OA,H2OB), C2P(H2PA,H2PB), C2Q(H2QA,H2QB), C2R(H2RA,H2RB), C59A(H59C,
 H59D)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C38(H38A,H38B,
 H38C), C53(H53A,H53B,H53C), C60(H60A,H60B,H60C), C1M(H1MA,H1MB,H1MC), C1N(H1NA,
 H1NB,H1NC), C1O(H1OA,H1OB,H1OC), C1P(H1PA,H1PB,H1PC), C2S(H2SA,H2SB,H2SC),
 C2T(H2TA,H2TB,H2TC), C2U(H2UA,H2UB,H2UC), C2V(H2VA,H2VB,H2VC), C60A(H60D,H60E,
 H60F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              2716
_shelx_hkl_checksum              13263
_shelx_fab_checksum              43268
_olex2_submission_special_instructions 'No special instructions were received'