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_1572625
_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
'C51 H57 N9, 1.012(C H2 Cl2), 1.627(C H4 O), 1.403(H2 O1), 0.404(O)'
_chemical_formula_sum            'C53.64 H68.34 Cl2.02 N9 O3.43'
_chemical_formula_weight         965.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-01-17
_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                90
_cell_angle_beta                 116.0400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9701(3)
_cell_length_b                   24.0962(6)
_cell_length_c                   15.7004(4)
_cell_measurement_reflns_used    9318
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      78.97
_cell_measurement_theta_min      4.83
_cell_volume                     5088.6(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  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON II CPAD area detector'
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Single Source'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            120441
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         3.402
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec ImuS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0891 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.8921.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             2060
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     713
_refine_ls_number_reflns         10976
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0673P)^2^+3.1350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10227
_reflns_number_total             10976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05236f2.cif
_cod_data_source_block           2094
_cod_depositor_comments
'Adding full bibliography for 1572625--1572628.cif.'
_cod_database_code               1572625
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.694
_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) groups, All O(H,H) groups
2. Restrained distances
 O93-H93B = O93-H93A
 0.87 with sigma of 0.02
 O91-H91B = O91-H91A
 0.87 with sigma of 0.02
 Cl75-C74 = Cl76-C74
 1.75 with sigma of 0.02
 O81-C82 = O83-C84 = O85-C86
 1.4 with sigma of 0.01
 H93B-H93A
 1.39 with sigma of 0.04
 H91B-H91A
 1.39 with sigma of 0.04
 Cl76-Cl75
 2.9 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl76 \\sim C74 \\sim Cl75: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O81 \\sim C82 \\sim O83 \\sim C84 \\sim O94: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C74, Cl76, Cl75
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(O83)+Sof(H83)+Sof(C84)+Sof(H84A)+Sof(H84B)+Sof(H84C)]+1*[Sof(O94)]+1*
 [Sof(O81)+Sof(H81)+Sof(C82)+Sof(H82A)+Sof(H82B)+Sof(H82C)]=1 with esd of 0
 Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(Cl72)=Sof(Cl73)=FVAR(1)
 Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(Cl75)=Sof(Cl76)=FVAR(2)
 Sof(O85)=Sof(H85)=Sof(C86)=Sof(H86A)=Sof(H86B)=Sof(H86C)=FVAR(3)
 Sof(O91)=Sof(H91A)=Sof(H91B)=FVAR(4)
 Sof(O93)=Sof(H93A)=Sof(H93B)=FVAR(5)
 Sof(O81)=Sof(H81)=Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(H82C)=FVAR(6)
 Sof(O83)=Sof(H83)=Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(H84C)=FVAR(7)
6.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B), C37(H37A,H37B), C39(H39A,
 H39B), C41(H41A,H41B), C51(H51A,H51B), C53(H53A,H53B), C55(H55A,H55B),
 C57(H57A,H57B), C59(H59A,H59B), C61(H61A,H61B), C71(H71A,H71B), C74(H74A,H74B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C22(H22), C24(H24), C26(H26), C27(H27), C28(H28)
6.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C58(H58A,H58B,
 H58C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C), C82(H82A,H82B,H82C), C84(H84A,
 H84B,H84C), C86(H86A,H86B,H86C)
6.d Idealised tetrahedral OH refined as rotating group:
 O81(H81), O83(H83), O85(H85)
;
_shelx_res_checksum              94519
_shelx_hkl_checksum              24324
_olex2_submission_special_instructions 'No special instructions were received'