Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding.
Yao, Huan; Ke, Hua; Zhang, Xiaobin; Pan, San-Jiang; Li, Ming-Shuang; Yang, Liu-Pan; Schreckenbach, Georg; Jiang, Wei; Journal of the American Chemical Society 140 (2018) 13466–13477; doi:10.1021/jacs.8b09157

data_4133268
_publ_section_title
;
 Molecular Recognition of Hydrophilic Molecules in Water by Combining the
 Hydrophobic Effect with Hydrogen Bonding.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13466
_journal_page_last               13477
_journal_paper_doi               10.1021/jacs.8b09157
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C66 H66 N2 O10, C3 H6 O3'
_chemical_formula_sum            'C69 H72 N2 O13'
_chemical_formula_weight         1137.28
_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     dual
_audit_creation_date             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                112.660(3)
_cell_angle_beta                 111.734(3)
_cell_angle_gamma                96.511(2)
_cell_formula_units_Z            1
_cell_length_a                   11.6154(5)
_cell_length_b                   12.7648(5)
_cell_length_c                   13.8417(6)
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    160.0
_cell_measurement_theta_max      59.07
_cell_measurement_theta_min      3.88
_cell_volume                     1678.92(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      160.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13923
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        57.893
_diffrn_reflns_theta_max         57.893
_diffrn_reflns_theta_min         3.878
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0823 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.8850. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1113
_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^)+(0.1700P)^2^+3.5520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3102
_refine_ls_wR_factor_ref         0.3342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3219
_reflns_number_total             4606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09157_si_006.cif
_cod_data_source_block           p-1_a
_cod_original_cell_volume        1678.91(13)
_cod_database_code               4133268
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 O7-C35
 1.15 with sigma of 0.02
 C35-O6
 1.38 with sigma of 0.02
 O6-C34
 1.38 with sigma of 0.02
 C35-O8
 1.38 with sigma of 0.02
 O8-C36
 1.38 with sigma of 0.02
 C35-C36
 2.54 with sigma of 0.04
 C35-C34
 2.54 with sigma of 0.04
 O8-O6
 2.7 with sigma of 0.04
 O7-O8
 2.54 with sigma of 0.04
 O7-O6
 2.54 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C35) = Uanis(C34)
Uanis(C36) = Uanis(C35)
Uanis(C36) = Uanis(C19)
Uanis(O7) = Uanis(C35)
Uanis(C17) = Uanis(C16)
Uanis(O6) = Uanis(O7)
Uanis(O6) = Uanis(C35)
Uanis(O8) = Uanis(C36)
Uanis(C35) = Uanis(O8)
Uanis(O7) = Uanis(O8)
Uanis(O6) = Uanis(O8)
Uanis(C34) = Uanis(O8)
4. Others
 Sof(O5B)=1-FVAR(1)
 Sof(O5A)=FVAR(1)
 Fixed Sof: H14A(0.5) H14B(0.5) H15A(0.5) H15B(0.5) C34(0.5) H34A(0.5)
 H34B(0.5) H34C(0.5) C35(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) O6(0.5)
 O7(0.5) O8(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C23(H23), C24(H24), C28(H28), C29(H29),
 N1(H1A)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C)
;
_olex2_submission_special_instructions 'No special instructions were received'