Charge-assisted hydrogen bonding in a bicyclic amide cage: an effective approach to anion recognition and catalysis in water.
Xu, Chengkai; Tran, Quy Gia; Liu, Dexin; Zhai, Canjia; Wojtas, Lukasz; Liu, Wenqi; Chemical science 15 (2024) 16040–16049; doi:10.1039/d4sc05236f

data_1572626
_publ_section_title
;
 Charge-assisted hydrogen bonding in a bicyclic amide cage: an effective
 approach to anion recognition and catalysis in water.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16040
_journal_page_last               16049
_journal_paper_doi               10.1039/d4sc05236f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety
'C54 H66 N9 O6, 3(Cl), 4.764(O), 1.651(C2 H6 O S)'
_chemical_formula_sum            'C57.3 H75.9 Cl3 N9 O12.41 S1.65'
_chemical_formula_weight         1248.66
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                67.614(3)
_cell_angle_beta                 81.558(3)
_cell_angle_gamma                68.560(3)
_cell_formula_units_Z            2
_cell_length_a                   14.9459(6)
_cell_length_b                   15.2203(7)
_cell_length_c                   18.4006(8)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    107.00
_cell_measurement_theta_max      57.22
_cell_measurement_theta_min      2.60
_cell_volume                     3602.4(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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      107.00
_diffrn_detector                 'Bruker PHOTON III CPAD area detector'
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Dual Source'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        49.750
_diffrn_reflns_theta_max         49.750
_diffrn_reflns_theta_min         2.597
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec ImuS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_T_max  0.7379
_exptl_absorpt_correction_T_min  0.5661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1279 before and 0.1049 after correction.
The Ratio of minimum to maximum transmission is 0.7672.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1319
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     815
_refine_ls_number_reflns         7315
_refine_ls_number_restraints     1269
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.1361
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3432
_refine_ls_wR_factor_ref         0.3934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4026
_reflns_number_total             7315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05236f2.cif
_cod_data_source_block           117_4_3
_cod_depositor_comments
'Adding full bibliography for 1572625--1572628.cif.'
_cod_original_formula_sum        'C57.30 H75.90 Cl3 N9 O12.41 S1.65'
_cod_database_code               1572626
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.921
_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
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 0.5*[Sof(Cl45)]+1*[Sof(Cl41)]+1*[Sof(Cl43)]+1*[Sof(Cl44)]+1*[Sof(Cl42)]+1*
 [Sof(Cl46)]=3 with esd of 0
 Sof(S)=Sof(O)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H2C)=FVAR(7)
 Sof(S)=Sof(O)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H2C)=FVAR(8)
 Sof(S)=Sof(O)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H2C)=FVAR(9)
 Sof(S)=Sof(O)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 Sof(H1C)=FVAR(10)
 Sof(S)=Sof(O)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H2C)=FVAR(11)
 Fixed Sof: O52(0.5) O54(0.5) O55(0.5) O56(0.5) O57(0.333333) O58(0.5)
 O59(0.333333)
6.a Secondary CH2 refined with riding coordinates:
 C21D(H21A,H21B), C23D(H23A,H23B), C25D(H25A,H25B), C27D(H27A,H27B), C29D(H29A,
 H29B), C31D(H31A,H31B), C21E(H21C,H21D), C23E(H23C,H23D), C25E(H25C,H25D),
 C27E(H27C,H27D), C29E(H29C,H29D), C31E(H31C,H31D)
6.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C1(H1A,
 H1B,H1C), C2(H2A,H2B,H2C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C)
6.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C7A(H7A), C3B(H3B), C5B(H5B), C7B(H7B), C3C(H3C),
 C5C(H5C), C7C(H7C), N22D(H22D), N24D(H24D), N26D(H26D), N22E(H22E), N24E(H24E),
  N26E(H26E)
6.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C28D(H28A,H28B,
 H28C), C30D(H30A,H30B,H30C), C32D(H32A,H32B,H32C), C28E(H28D,H28E,H28F),
 C30E(H30D,H30E,H30F), C32E(H32D,H32E,H32F)
;
_shelx_res_checksum              17800
_shelx_hkl_checksum              5557
_olex2_submission_special_instructions 'No special instructions were received'