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_4133261
_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 H8 O2'
_chemical_formula_sum            'C69 H74 N2 O12'
_chemical_formula_weight         1123.30
_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             2017-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                91.122(4)
_cell_angle_beta                 92.400(3)
_cell_angle_gamma                103.052(4)
_cell_formula_units_Z            1
_cell_length_a                   11.9576(10)
_cell_length_b                   12.1300(10)
_cell_length_c                   12.1777(10)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    160.0
_cell_measurement_theta_max      58.98
_cell_measurement_theta_min      3.63
_cell_volume                     1718.4(2)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      160.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14518
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        58.975
_diffrn_reflns_theta_max         58.975
_diffrn_reflns_theta_min         3.634
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0840 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.7956. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0680P)^2^+1.6590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4382
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09157_si_005.cif
_cod_data_source_block           p-1
_cod_database_code               4133261
_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
 C33-O7
 1.42 with sigma of 0.02
 O8-C34
 1.42 with sigma of 0.02
 C34-O8
 1.42 with sigma of 0.02
 C35-O8
 1.42 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O8) = Uanis(O7)
Uanis(C34) = Uanis(C33)
Uanis(O6) = Uanis(O5)
Uanis(C35) = Uanis(C34)
4. Others
 Fixed Sof: O5(0.5) O6(0.5) H5A(0.5) H5B(0.5) H6A(0.5) H6B(0.5) C35(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5) O7(0.5) O8(0.5) C33(0.5) H33A(0.5) H33B(0.5)
 H33C(0.5) C34(0.5) H34A(0.5) H34B(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B), C27(H5A,H5B),
 C28(H6A,H6B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C34(H34A,H34B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C10(H10), C11(H11), C19(H19), C20(H20), C25(H25),
 C26(H26)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C33(H33A,H33B,
 H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'