From small changes to big gains: pyridinium-based tetralactam macrocycle for enhanced sugar recognition in water.
Zhai, Canjia; Zulueta, Ethan Cross; Mariscal, Alexander; Xu, Chengkai; Cui, Yunpeng; Wang, Xudong; Wu, Huang; Doan, Carson; Wojtas, Lukasz; Zhang, Haixin; Cai, Jianfeng; Ye, Libin; Wang, Kun; Liu, Wenqi; Chemical science 15 (2024) 19588–19598; doi:10.1039/d4sc06190j

data_1573054
_publ_section_title
;
 From small changes to big gains: pyridinium-based tetralactam macrocycle
 for enhanced sugar recognition in water.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              19588
_journal_page_last               19598
_journal_paper_doi               10.1039/d4sc06190j
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety
'C48 H40 N6 O4, C6 H12 O6, 2(Cl), 5.279(H2 O), 0.535(O)'
_chemical_formula_sum            'C54 H62.56 Cl2 N6 O15.82'
_chemical_formula_weight         1119.59
_chemical_name_systematic        Glucose-BPAT
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-30 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.7740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.4244(4)
_cell_length_b                   13.2628(2)
_cell_length_c                   16.6870(2)
_cell_measurement_reflns_used    9631
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      78.82
_cell_measurement_theta_min      3.41
_cell_volume                     5159.85(14)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_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 0.984
_diffrn_measurement_device       'kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            55151
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.074
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0862 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.8724.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             2356
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 4549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         10690
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0807P)^2^+2.0653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                10215
_reflns_number_total             10690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06190j2.cif
_cod_data_source_block           D116
_cod_depositor_comments          'Adding full bibliography for 1573054.cif.'
_cod_original_cell_volume        5159.84(13)
_cod_database_code               1573054
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.931
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O71-H71B = O71-H71A
 0.88 with sigma of 0.02
 O72-H72B = O72-H72A
 0.88 with sigma of 0.02
 H72B-O73
 1.9 with sigma of 0.02
 O73-H73A = O73-H73B
 0.88 with sigma of 0.02
 O74-H74A = O74-H74B
 0.88 with sigma of 0.01
 O75-H75
 0.88 with sigma of 0.02
 O76-H76A = O76-H76B
 0.88 with sigma of 0.02
 H76B-H49
 -2.2 with sigma of 0.02
 O78-H78A = O78-H78B
 0.88 with sigma of 0.02
 H71B-H71A
 1.4 with sigma of 0.04
 H72A-H72B
 1.4 with sigma of 0.04
 H73B-H73A
 1.4 with sigma of 0.04
 H74B-H74A
 1.4 with sigma of 0.02
 H75-H75_$1
 1.4 with sigma of 0.04
 H76A-H76B
 1.4 with sigma of 0.04
 H78A-H78B
 1.4 with sigma of 0.04
3. Others
 1*[Sof(Cl64)]+1*[Sof(Cl63)]+1*[Sof(Cl62)]+1*[Sof(Cl61)]=2 with esd of 0
 Sof(O73)=Sof(H73A)=Sof(H73B)=FVAR(5)
 Sof(O71)=Sof(H71A)=Sof(H71B)=FVAR(6)
 Sof(O74)=Sof(H74A)=Sof(H74B)=FVAR(7)
 Sof(O77)=1-FVAR(8)
 Sof(O76)=Sof(H76A)=Sof(H76B)=FVAR(8)
 Sof(O75)=0.5*FVAR(10)
 Sof(H75)=FVAR(9)
 Sof(O72)=Sof(H72A)=Sof(H72B)=FVAR(10)
 Sof(O79)=1-FVAR(11)
 Sof(O78)=Sof(H78A)=Sof(H78B)=FVAR(11)
4.a Ternary CH refined with riding coordinates:
 C43(H43), C45(H45), C46(H46), C47(H47), C48(H48)
4.b Secondary CH2 refined with riding coordinates:
 C22C(H22A,H22B), C24C(H24A,H24B), C22D(H22C,H22D), C24D(H24C,H24D), C42(H42A,
 H42B)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C7A(H7A), C3B(H3B), C5B(H5B), C7B(H7B), N21C(H21C),
 N23C(H23C), C27C(H27C), C28C(H28C), C29C(H29C), C30C(H30C), C34C(H34C),
 C35C(H35C), C36C(H36C), C37C(H37C), N21D(H21D), N23D(H23D), C27D(H27D),
 C28D(H28D), C29D(H29D), C30D(H30D), C34D(H34D), C35D(H35D), C36D(H36D),
 C37D(H37D)
4.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
4.e Idealised tetrahedral OH refined as rotating group:
 O41(H41), O49(H49), O50(H50), O51(H51), O52(H52)
;
_shelx_res_checksum              30684
_shelx_hkl_checksum              46094
_olex2_submission_special_instructions 'No special instructions were received'