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_4133260
_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, C4 H8 O2'
_chemical_formula_sum            'C70 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             2017-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                111.697(4)
_cell_angle_beta                 112.056(5)
_cell_angle_gamma                96.412(4)
_cell_formula_units_Z            1
_cell_length_a                   11.6938(8)
_cell_length_b                   12.6480(10)
_cell_length_c                   13.6896(9)
_cell_measurement_reflns_used    5293
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      58.88
_cell_measurement_theta_min      3.90
_cell_volume                     1668.2(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD 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  0.0284
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10876
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        54.242
_diffrn_reflns_theta_max         54.242
_diffrn_reflns_theta_min         3.895
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0717 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8834. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.205
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.560
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.572
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.1086
_refine_ls_shift/su_max          0.001
_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          0.3536
_refine_ls_wR_factor_ref         0.3736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2971
_reflns_number_total             4026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09157_si_008.cif
_cod_data_source_block           p-1_a
_cod_database_code               4133260
_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 C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37 = C35-C34
 1.53 with sigma of 0.02
 O7-C36
 1.2 with sigma of 0.02
 O6-C35
 1.42 with sigma of 0.02
 O6-C36
 1.38 with sigma of 0.02
 C32B-C31B
 1.54 with sigma of 0.02
 C32A-C31A
 1.54 with sigma of 0.02
 C31B-C30
 1.54 with sigma of 0.02
 C30-C31A
 1.54 with sigma of 0.02
 C32A-C33A
 1.54 with sigma of 0.02
 C32B-C33B
 1.54 with sigma of 0.02
 O7-O6
 2.3 with sigma of 0.04
 C34-O6
 2.4 with sigma of 0.04
 C37-O7
 2.3 with sigma of 0.04
 C30-C32B
 2.54 with sigma of 0.04
 C30-C32A
 2.54 with sigma of 0.04
 C31B-C33B
 2.54 with sigma of 0.04
 C31A-C33A
 2.54 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C37 \\sim C34 \\sim O7 \\sim C36 \\sim O6 \\sim C35: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C32B) = Uanis(C33B)
Uanis(C32B) = Uanis(C32A)
Uanis(C32A) = Uanis(C33A)
Uanis(C32A) = Uanis(C33A) = Uanis(C32B) = Uanis(C33B)
4. Others
 Fixed Sof: H18a(0.5) H18b(0.5) H19a(0.5) H19b(0.5) H30a(0.5) H30b(0.5)
 H30c(0.5) H30d(0.5) C31A(0.5) H31a(0.5) H31b(0.5) C31B(0.5) H31c(0.5)
 H31d(0.5) C32A(0.5) H32a(0.5) H32b(0.5) C32B(0.5) H32c(0.5) H32d(0.5)
 C33A(0.5) H33a(0.5) H33b(0.5) H33c(0.5) C33B(0.5) H33d(0.5) H33e(0.5)
 H33f(0.5) O5A(0.5) O5B(0.5) C34(0.5) H34a(0.5) H34b(0.5) H34c(0.5) C35(0.5)
 H35a(0.5) H35b(0.5) C36(0.5) C37(0.5) H37a(0.5) H37b(0.5) H37c(0.5) O6(0.5)
 O7(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), C18(H18a,H18b),
 C19(H19a,H19b), C30(H30a,H30b), C30(H30c,H30d), C31A(H31a,H31b), C31B(H31c,
 H31d), C32A(H32a,H32b), C32B(H32c,H32d), C35(H35a,H35b)
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:
 C17(H17a,H17b,H17c), C33A(H33a,H33b,H33c), C33B(H33d,H33e,H33f), C34(H34a,
 H34b,H34c), C37(H37a,H37b,H37c)
;
_olex2_submission_special_instructions 'No special instructions were received'